I have another challenge proposal. This time with a twist.

Starting Timeline:
1) You are inserted into one of either ASWaH!Prime timeline at the start date of the first update. Nothing is guaranteed, the timeline isn't sacrosanct and the smallest action can have incredible repercussions down the road.
2) You are inserted shortly after Viserys has annexed most of the major political entities west of the Bone Mountains aside from Yi Ti which he is still subtly influencing, or else rendered them Protectorates in all but name. I would say this is a few short years before thing get incredibly hairy for the main cast, but they are certainly on a very long winning streak, but consequently they are full up on all kinds of new allies you've never seen before and your conditional bargaining position is even less than some of the other challenges presented here, depending on your approach.
3) You are inserted into canon at the Quest's start date. Magic has awakened earlier than usual. Things are very different, but as @Goldfish states, the Planes are mostly functional, Asmodeus isn't currently too busy WINNING to care what you think, and there is no Void. All apocalypses in the grand scheme of things, even ones that swallow entire planets, aren't completely guaranteed to ruin your fun.

Starting Locations:
1) You can start in any major population center, but you just did something to severely shake things up and accumulate memories of what it was over the course of the next week. By that point trouble will have likely caught up with you unless you were incredibly careful as a matter of course.
2) You start scattered throughout Planetos. More on this later. But you accrue Double the value of any Benefits mentioned later on individually.
3) You start scattered throughout the Planes, but accrue triple the Benefits mentioned later on.

Starting Conceit:
1) You can pick eleven other people from the thread to accompany you into your challenge. However, they acquire all of the same Benefits that you yourself do. Alternatively, you can pick some people from other boards if you happen to find them more trustworthy or just easier to get along with.
2) You can select eleven other characters from popular fiction to accompany you into your challenge, though without any of their base abilities if they should possess them, they will in essence remain themselves. They can be Composite type characters, having the parts which make them worldly, experienced or just the most useful version of themselves to you at that time, or they can be drawn from a particular point in their personal journey. They are aware of the stakes of the challenge and have provisionally accepted your invitation to work together, but they are their own person and their motives will inform on their decisions taken once the challenge begins. This excludes ASWaH!Prime characters. As above, they share every Benefit that you yourself do, at the cost of 1/2th effectiveness.
3) You can select a mix of the two above, people from real life to stack the deck if you're an extrovert who has a better read on family or friends, or even ASWaH!Prime characters. As above, they share all Benefits you yourself do, at the cost of 1/3rd effectiveness.

Starting Benefits
1) You gain one level up to 20 every year, and it is additive with your current XP, not accumulative up to the cap. So your progress isn't reset in the middle of some heavy adventuring, nor are you given disincentive either way to accumulate more XP. This rate can be doubled or even tripled depending on your previous selections, or alternatively halved or cut down to a third of the stated Benefit.
2) You can choose whatever template or starting race you feel like, but also have to pay off the level adjustment out of the above Benefit. You can only choose one, however, you can select a Race and a Template if you chose Location 3 and Conceit 3.
2.1) Feat, race and class selection is fairly generous for first level. Wedded to history? Grab it now if you want it, because you can't get it later. Rare race or template? Same deal, barring what you could reasonably acquire in-challenge due to your own efforts.
2.2) Elite Array is yes if you select condition #1 for Locations. 32 Point Buy for Condition #2. 36 Point Buy if you opt for Condition #3.
3) You can only qualify for PrCs if you meet the requisites, but there is absolutely nothing stopping you from retraining at any point you gain the first Benefit, at least until Level 20. After which, you can only retrain "a sane" amount as would reasonably be believable, typically one retroactive decision a year, like swapping feats that aren't locked in due to pre-requisites of a class or which were granted because of a Wish or Miracle or similar circumstances, those being metaphysically "bonded" with you, or retraining a PRC, so long as you don't lose the prerequisites which allowed your entrance to the first level until you are ready to leave it.

Starting Challenges:
1) Asmodeus is "indisposed", Baator is currently in the middle of a Cold War, and Avernus has been taken for keeps by Tiamat. Many of the Archdukes are kept from maneuvering to take over due to having to keep the course of the Blood War from reversing, as Tiamat has co-opted considerable resources and metaphysically taken hold of the Plane, and is directing all of it towards her own goals. The center-point of your challenge will inevitably draw you into this plot-line whether you like it or not, though the degree to which it effects you depends on your starting Timeline.
2) Many Gods become aware of your presence and some subtle alterations to events fated to take place due to it. No more of an advantage than they might gain after you have made several moves in the board, but chances are you will get wrapped up in some kind of shenanigans due to this whether you like it or not. You are too interesting to ignore now.
3) A Negaverse Rift Opens! A "Counter Group" is inserted along with yours! They're all oddly familiar, oh wait, THEY'RE YOU! What madness will this entail? Find out, next time on Dragon Ball Z!
 
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Good. I would absolutely hate the "you must defeat your dark reflections!" thing.

When you say canon for start 3, do you mean ASOIAF canon?
More @Goldfish's Composite Canon. Everything is as per canon, until you Insert, which is where "functional Great Wheel planar cosmology" mechanisms kick in and everyone starts slowly peering over going "oh what's dis". Whether or not there was a sort of "sundering" stand-in event which cut off Planetos from the Planes, or whether it was ONLY the planet that was isolated I will leave to the interpretation of the challenged, since it's obviously not incredibly relevant outside of more long-term implications, which isn't really the point of the challenge anyway.
 
I have another challenge proposal. This time with a twist.

Starting Timeline:
1) You are inserted into one of either ASWaH!Prime timeline at the start date of the first update. Nothing is guaranteed, the timeline isn't sacrosanct and the smallest action can have incredible repercussions down the road.
2) You are inserted shortly after Viserys has annexed most of the major political entities west of the Bone Mountains aside from Yi Ti which he is still subtly influencing, or else rendered them Protectorates in all but name. I would say this is a few short years before thing get incredibly hairy for the main cast, but they are certainly on a very long winning streak, but consequently they are full up on all kinds of new allies you've never seen before and your conditional bargaining position is even less than some of the other challenges presented here, depending on your approach.
3) You are inserted into canon at the Quest's start date. Magic has awakened earlier than usual. Things are very different, but as @Goldfish states, the Planes are mostly functional, Asmodeus isn't currently too busy WINNING to care what you think, and there is no Void. All apocalypses in the grand scheme of things, even ones that swallow entire planets, aren't completely guaranteed to ruin your fun.

Starting Locations:
1) You can start in any major population center, but you just did something to severely shake things up and accumulate memories of what it was over the course of the next week. By that point trouble will have likely caught up with you unless you were incredibly careful as a matter of course.
2) You start scattered throughout Planetos. More on this later. But you accrue Double the value of any Benefits mentioned later on individually.
3) You start scattered throughout the Planes, but accrue triple the Benefits mentioned later on.

Starting Conceit:
1) You can pick eleven other people from the thread to accompany you into your challenge. However, they acquire all of the same Benefits that you yourself do. Alternatively, you can pick some people from other boards if you happen to find them more trustworthy or just easier to get along with.
2) You can select eleven other characters from popular fiction to accompany you into your challenge, though without any of their base abilities if they should possess them, they will in essence remain themselves. They can be Composite type characters, having the parts which make them worldly, experienced or just the most useful version of themselves to you at that time, or they can be drawn from a particular point in their personal journey. They are aware of the stakes of the challenge and have provisionally accepted your invitation to work together, but they are their own person and their motives will inform on their decisions taken once the challenge begins. This excludes ASWaH!Prime characters. As above, they share every Benefit that you yourself do, at the cost of 1/2th effectiveness.
3) You can select a mix of the two above, people from real life to stack the deck if you're an extrovert who has a better read on family or friends, or even ASWaH!Prime characters. As above, they share all Benefits you yourself do, at the cost of 1/3rd effectiveness.

Starting Benefits
1) You gain one level up to 20 every year, and it is additive with your current XP, not accumulative up to the cap. So your progress isn't reset in the middle of some heavy adventuring, nor are you given disincentive either way to accumulate more XP. This rate can be doubled or even tripled depending on your previous selections, or alternatively halved or cut down to a third of the stated Benefit.
2) You can choose whatever template or starting race you feel like, but also have to pay off the level adjustment out of the above Benefit. You can only choose one, however, you can select a Race and a Template if you chose Location 3 and Conceit 3.
2.1) Feat, race and class selection is fairly generous for first level. Wedded to history? Grab it now if you want it, because you can't get it later. Rare race or template? Same deal, barring what you could reasonably acquire in-challenge due to your own efforts.
2.2) Elite Array is yes if you select condition #1 for Locations. 32 Point Buy for Condition #2. 36 Point Buy if you opt for Condition #3.
3) You can only qualify for PrCs if you meet the requisites, but there is absolutely nothing stopping you from retraining at any point you gain the first Benefit, at least until Level 20. After which, you can only retrain "a sane" amount as would reasonably be believable, typically one retroactive decision a year, like swapping feats that aren't locked in due to pre-requisites of a class or which were granted because of a Wish or Miracle or similar circumstances, those being metaphysically "bonded" with you, or retraining a PRC, so long as you don't lose the prerequisites which allowed your entrance to the first level until you are ready to leave it.

Starting Challenges:
1) Asmodeus is "indisposed", Baator is currently in the middle of a Cold War, and Avernus has been taken for keeps by Tiamat. Many of the Archdukes are kept from maneuvering to take over due to having to keep the course of the Blood War from reversing, as Tiamat has co-opted considerable resources and metaphysically taken hold of the Plane, and is directing all of it towards her own goals. The center-point of your challenge will inevitably draw you into this plot-line whether you like it or not, though the degree to which it effects you depends on your starting Timeline.
2) Many Gods become aware of your presence and some subtle alterations to events fated to take place due to it. No more of an advantage than they might gain after you have made several moves in the board, but chances are you will get wrapped up in some kind of shenanigans due to this whether you like it or not. You are too interesting to ignore now.
3) A Negaverse Rift Opens! A "Counter Group" is inserted along with yours! They're all oddly familiar, oh wait, THEY'RE YOU! What madness will this entail? Find out, next time on Dragon Ball Z!
Responding to my own challenge early, because it be like that, it really do.

Selections below...

Timeline: I pick #3, but not really because I'm planning to take it easy explicitly or rest on my laurels, I certainly don't plan on fixing all the problems by myself, but the challenge itself basically forces you to be at least somewhat proactive no matter what you choose.

Location: I pick #3 again, mostly because I absolutely need that leg-up from the Benefits due to my other selections costing me a nerf to my level gain. It's a bit more risky since I don't know where I'll end up, but you can assume from my own selection and having written the challenge, the randomness to it isn't a death sentence, just not incredibly convenient compared to starting all in the same location as in Option #1 or on the same plane as in #2.

Conceit: I pick #3, as I am taking Viserys and every Companion except Rina, mostly because there just wasn't enough room, and sorry to say, she's pragmatically just about the only companion who isn't in some way essential. While her abilities in ASWaH and her circumstances provide considerable benefit, none of that matters given the stated rules of the challenge, and presumably her Canon self is still in White Harbor and can be helped later on to assuage any of the guilt I feel for leaving her out. They are going to be Composited characters, having all of the worldly experience of a group of people who have survived the Long Night, adventuring, intrigue, political master-minding and Keikaku Doori being incredibly passe and old hat to them, but not ancient eldritch beings who I can't hope to comprehend. Just people used to wielding a lot of power very responsibly (for the most part, anyway).

Benefit Usage: I'm just going to state here since I didn't in my main challenge, but you can't be an Epic Dragon, and presumably you shouldn't choose to be some other incredibly bullshit race that doesn't even need levels to obliterate half the setting from point of insertion. However, most everything else is free game. Be somewhat reasonable and remember... picking a dragon means you start around your current age, if that, and have advanced that far in age category. Blatantly unfair to those who aren't fifty or more years old IRL.

For example, at my age I just barely miss starting as a Juvenile Red Dragon. My LA is 6 already. I also choose the Mighty Template. I'm not quite sure how to determine LA from that alone, but I would say it is considerable, maybe double value, as I am already beefy as hell due to it. +130 HP, SR, heaps of bonuses, and my spell saves are way better, for what good it does me right now, as I only cast as a 1st Level Sorcerer. It will take me at least twelve years to pay off most of this, but I'm mostly picking it because I do not know where I will end up, and I will need the survivability. Also kind of nervous about mind control, so this neatly sidesteps that even starting with no equipment.

It will take at least a dozen years to pay off that nasty LA before I start treading water towards virtual Godhood, though. OTOH, everyone else should be archmages or nigh-unkillable champions, presuming they survived and flourished out in the Planes. I will spend most of my time gathering the resources necessary to link up with everyone/help re-consolidate.

After which I will mostly chill out, as there is little I will not be able to achieve in just a few short decades. I also do not have to stress about coming up with long term plans, though I will probably choose to become a Theurge-ish build like Lya so that I can make use of All of the Magic. I am already a murder machine otherwise, and there is no guarantee I will push myself enough to become Mythic. Luckily it doesn't matter, I will already be a high CR threat in a few centuries with 20 PC levels and heaps of racial HD from dragon aging.

By the time I am a Great Wyrm, I will quite literally be on-par with a Major Godly Avatar, not just an Elemental Ruler like the Sultana, Brass Bastard, etc. Not quite certain on the feats and stuff.
 
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I have another challenge proposal. This time with a twist.

Starting Timeline:
1) You are inserted into one of either ASWaH!Prime timeline at the start date of the first update. Nothing is guaranteed, the timeline isn't sacrosanct and the smallest action can have incredible repercussions down the road.
2) You are inserted shortly after Viserys has annexed most of the major political entities west of the Bone Mountains aside from Yi Ti which he is still subtly influencing, or else rendered them Protectorates in all but name. I would say this is a few short years before thing get incredibly hairy for the main cast, but they are certainly on a very long winning streak, but consequently they are full up on all kinds of new allies you've never seen before and your conditional bargaining position is even less than some of the other challenges presented here, depending on your approach.
3) You are inserted into canon at the Quest's start date. Magic has awakened earlier than usual. Things are very different, but as @Goldfish states, the Planes are mostly functional, Asmodeus isn't currently too busy WINNING to care what you think, and there is no Void. All apocalypses in the grand scheme of things, even ones that swallow entire planets, aren't completely guaranteed to ruin your fun.

Starting Locations:
1) You can start in any major population center, but you just did something to severely shake things up and accumulate memories of what it was over the course of the next week. By that point trouble will have likely caught up with you unless you were incredibly careful as a matter of course.
2) You start scattered throughout Planetos. More on this later. But you accrue Double the value of any Benefits mentioned later on individually.
3) You start scattered throughout the Planes, but accrue triple the Benefits mentioned later on.

Starting Conceit:
1) You can pick eleven other people from the thread to accompany you into your challenge. However, they acquire all of the same Benefits that you yourself do. Alternatively, you can pick some people from other boards if you happen to find them more trustworthy or just easier to get along with.
2) You can select eleven other characters from popular fiction to accompany you into your challenge, though without any of their base abilities if they should possess them, they will in essence remain themselves. They can be Composite type characters, having the parts which make them worldly, experienced or just the most useful version of themselves to you at that time, or they can be drawn from a particular point in their personal journey. They are aware of the stakes of the challenge and have provisionally accepted your invitation to work together, but they are their own person and their motives will inform on their decisions taken once the challenge begins. This excludes ASWaH!Prime characters. As above, they share every Benefit that you yourself do, at the cost of 1/2th effectiveness.
3) You can select a mix of the two above, people from real life to stack the deck if you're an extrovert who has a better read on family or friends, or even ASWaH!Prime characters. As above, they share all Benefits you yourself do, at the cost of 1/3rd effectiveness.

Starting Benefits
1) You gain one level up to 20 every year, and it is additive with your current XP, not accumulative up to the cap. So your progress isn't reset in the middle of some heavy adventuring, nor are you given disincentive either way to accumulate more XP. This rate can be doubled or even tripled depending on your previous selections, or alternatively halved or cut down to a third of the stated Benefit.
2) You can choose whatever template or starting race you feel like, but also have to pay off the level adjustment out of the above Benefit. You can only choose one, however, you can select a Race and a Template if you chose Location 3 and Conceit 3.
2.1) Feat, race and class selection is fairly generous for first level. Wedded to history? Grab it now if you want it, because you can't get it later. Rare race or template? Same deal, barring what you could reasonably acquire in-challenge due to your own efforts.
2.2) Elite Array is yes if you select condition #1 for Locations. 32 Point Buy for Condition #2. 36 Point Buy if you opt for Condition #3.
3) You can only qualify for PrCs if you meet the requisites, but there is absolutely nothing stopping you from retraining at any point you gain the first Benefit, at least until Level 20. After which, you can only retrain "a sane" amount as would reasonably be believable, typically one retroactive decision a year, like swapping feats that aren't locked in due to pre-requisites of a class or which were granted because of a Wish or Miracle or similar circumstances, those being metaphysically "bonded" with you, or retraining a PRC, so long as you don't lose the prerequisites which allowed your entrance to the first level until you are ready to leave it.

Starting Challenges:
1) Asmodeus is "indisposed", Baator is currently in the middle of a Cold War, and Avernus has been taken for keeps by Tiamat. Many of the Archdukes are kept from maneuvering to take over due to having to keep the course of the Blood War from reversing, as Tiamat has co-opted considerable resources and metaphysically taken hold of the Plane, and is directing all of it towards her own goals. The center-point of your challenge will inevitably draw you into this plot-line whether you like it or not, though the degree to which it effects you depends on your starting Timeline.
2) Many Gods become aware of your presence and some subtle alterations to events fated to take place due to it. No more of an advantage than they might gain after you have made several moves in the board, but chances are you will get wrapped up in some kind of shenanigans due to this whether you like it or not. You are too interesting to ignore now.
3) A Negaverse Rift Opens! A "Counter Group" is inserted along with yours! They're all oddly familiar, oh wait, THEY'RE YOU! What madness will this entail? Find out, next time on Dragon Ball Z!
Starting Timeline: Option 3 - I like my reality unfucked.

Starting Location: Option 3 - Fingers crossed everyone ends up in hospitable locales! Triple benefits are hard to turn down, though, along with being able to select race and template

Starting Conceit: Option 1 - I'm sure some of y'all would like to come along? I hope I would have the option to ask for willing participants, as I would hate to rip any of y'all from a mostly comfortable but mundane reality and deposit you in a D&D cosmology. A bit of time to plan a rendezvous point would be nice, too.

Starting Benefits: Full on 36 point but is nice, and I'm assuming races we must choose from are actual player races rather than creatures? If that's the case, I'm going Human, but if not I'll start as a Faerie Dragon instead. They're CR 3, but also start as 3rd level Sorcerers, which is nice because I intend to choose to be a Sorcerer, at least at first, which obviates some of the need to buy off the level adjustment. And I'm going to start with the Sublime Creature template. It'll greatly improve my survivability and comes with some nice quality of life options, including biological immortality.

Challenge: Option 1 - Tiamat having the level of influence and power is problematic, but it's better than Option 2's attention from a bunch of bored gods. That is how bad shit happens to you for no reason. And I have no interest in messing around with Nega-me or Nega-ya'll, so Option 3 is completely off the table.

EDIT: I see that we can start as anything we want, with some caveats based on age and sanity. In that case, I'm going with Mind Dragon and the Sublime Creature template. I would start as a CR 10 Young Adult Mind Dragon and would become an Adult in 24 more years, while the level adjustment should be bought off in no more than 4 years with the triple benefits accruing. This is a nice starting chassis and capable of survival just about anywhere.
 
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Starting Timeline: Option 3 - I like my reality unfucked.

Starting Location: Option 3 - Fingers crossed everyone ends up in hospitable locales! Triple benefits are hard to turn down, though, along with being able to select race and template

Starting Conceit: Option 1 - I'm sure some of y'all would like to come along? I hope I would have the option to ask for willing participants, as I would hate to rip any of y'all from a mostly comfortable but mundane reality and deposit you in a D&D cosmology. A bit of time to plan a rendezvous point would be nice, too.

Starting Benefits: Full on 36 point but is nice, and I'm assuming races we must choose from are actual player races rather than creatures? If that's the case, I'm going Human, but if not I'll start as a Faerie Dragon instead. They're CR 3, but also start as 3rd level Sorcerers, which is nice because I intend to choose to be a Sorcerer, at least at first, which obviates some of the need to buy off the level adjustment. And I'm going to start with the Sublime Creature template. It'll greatly improve my survivability and comes with some nice quality of life options, including biological immortality.

Challenge: Option 1 - Tiamat having the level of influence and power is problematic, but it's better than Option 2's attention from a bunch of bored gods. That is how bad shit happens to you for no reason. And I have no interest in messing around with Nega-me or Nega-ya'll, so Option 3 is completely off the table.
People are willing, as stated per the "fictional characters provisionally accepting of cooperation", implying everyone is coming along of their own free will. I am sure most of us would hesitate to risk a fate worse than death in a setting where even a functional after-life isn't necessarily a walk in the park, but for the sake of the challenge let us assume we all suffered enough ennui to grow just that bored of mundane life and modernity.

I would cruise around in the background generally doing all of the schmoozing. I would be very lazy about adventuring, but would be pathologically incapable of refusing to carry my own weight since I give into peer pressure very easily. I generally go into these challenges thinking "what's the quickest way to become a dragon" so I just decided not to short change myself, either, personally, but it does have the trade off that for like ten years or more I cannot gain any levels from lazing around, although starting off as a CR 12 dragon isn't anything to scoff at.
 
@Crake To clarify something, the only downside of starting with a strong race is having to spend your free 20 level ups on buying it off?

A Juvenile Red is ECL 22 from the get go, how does that work?
 
@Crake To clarify something, the only downside of starting with a strong race is having to spend your free 20 level ups on buying it off?

A Juvenile Red is ECL 22 from the get go, how does that work?
You actually gain your benefits continually so long as you have fewer than 20 character levels. So assuming you have a huge deficit due to higher ECL, you will continue to accrue benefits until you pay it off at the stated rate, at which point, upon paying it off, you will then gain up to 20 character levels, again at the stated rate.
 
One could pick Paragon Black Ethergaunt or Paragon Solar, and still get those twenty free levels eventually? Ok.

Assuming something saner, the Mind Dragons offer amazing bang for your buck, but Golds are also pretty sweet, and presumably end up way higher on the power scale by the end. Something unusual and fun would be a Psionic Coatl. Or throw the Saint template on a White Ethergaunt for shits and giggles and confound the shit out of everyone who knows what Ethergaunts are.

The crunchy bits are just too open-ended right now.

I'm really not a fan of the "pick a ton of fictional characters".

Probably go with:
Starting Timeline: 3 - I'd like a non fucked reality, thank you.
Starting Location: 3 - Reality isn't fucked so why not explore, and this enables better starting stats.
Starting Conceit: 3 - Why not?
Starting Benefits: Paragon Solar. Gonna be paying off LA for a century, but who cares when you are a Paragon Solar?
Challenge: 2 - It sounds like the Chinese kind of interesting.
 
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One could pick Paragon Black Ethergaunt or Paragon Solar, and still get those twenty free levels eventually? Ok.

Assuming something saner, the Mind Dragons offer amazing bang for your buck, but Golds are also pretty sweet, and presumably end up way higher on the power scale by the end. Something unusual and fun would be a Psionic Coatl. Or throw the Saint template on a White Ethergaunt for shits and giggles and confound the shit out of everyone who knows what Ethergaunts are.

The crunchy bits are just too open-ended right now.

I'm really not a fan of the "pick a ton of fictional characters".

Probably go with:
Starting Timeline: 3 - I'd like a non fucked reality, thank you.
Starting Location: 3 - Reality isn't fucked so why not explore, and this enables better starting stats.
Starting Conceit: 3 - Why not?
Starting Benefits: Paragon Solar. Gonna be paying off LA for a century, but who cares when you are a Paragon Solar?
Challenge: 2 - It sounds like the Chinese kind of interesting.
Damn, Paragon is bonkers. I didn't imagine there'd be many Templates that were just "Fuck it, the answer is YES" and most of the big ones would be similar in scale to Mighty.

Your Saint Ethergaunt idea was amusing to me.

I should probably consider some kind of limitation to Templates, since I was presuming you would not start off higher than CR 15, if that, to begin with. Though there are a variety of Templates that when stacked on top of character levels and a great chassis would already make you bullshit by the time you were done accruing your Benefits.

Anyway, I'm still keen on latitude for Races, even if most people decide to choose Outsiders because they're already optimal Dragons have a nicer payoff IMO. They can freely learn Cleric spells, so you could even mix Druid Casting with Arcane casting whilst still being able to gain Divine spells.

I'm tempted to say Dragons are a Yes, but Outsiders are a No. You are mainly supposed to experience an initial scramble while still hitting the ground running, or at best sprinting toward your goals, but a high-end Celestial or Fiend would mostly be at the top of the food chain already.

I'm really not a fan of the "pick a ton of fictional characters".

I was presuming there would be one person who would be like "But I don't want to bring any of these."

No, you can either pick a bunch of somewhat agreeable allies, or pick a bunch of thread-goers to see who can munchkin the hardest, or just a bunch of people you know since you're some kind of normal person with more than a handful of friends and family who would actually enjoy living the High Fantasy life. Though the conceit of the challenge is that rather than picking a dozen faceless peons, you would have an idea of who you'd bring with you to watch your back in a D&D setting.

Presuming everyone consolidated build options, you could legitimately start the challenge as a group of nascent godlings ready to clean up Westeros and Essos, or become high profile movers and shakers in the Planes.

Dollars to donuts a thread-centric party starts an industrial revolution within a decade.

Edit: Thinking about it, a good hard cap to this challenge would be to make the Benefits actually only go up to 20 free levels, at the stated rate. So you can either buy up to 20 Level Adjustment worth of Racial/Template(s), yeah you can take more than one if you plan on just using up all 20 at once, or you could take a race with no level adjustment and guarantee yourself 20 levels in as little as seven years with virtually no input from yourself.
 
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20 bucks says the Princess and the Dragon will have a tryst going by weeks end.

A polite dragon that not only considers her honor, but actually used discretion when talking about matter she'd rather keep private, and is a rather accomplished dragon if his throne is any indication?

It sounds like a goddamn YA novel plot, and I work in a library, I know my YA novel plots.
I wouldn't say so.

He is withholding something from her, basic enough that she's willing to pay in wishcraft for it.
Seems like a pretty normal hostage/abductor relation, which is not a good one?
 
It's not stupid so much as wasteful. Yes you can interrogate the witch, even burn a few spells in order to be sure you got all of her secrets, and then sacrifice her to the dragons.

Or, you can hire the lady, help her growth, reap the rewards of the new ways she finds to fuck shit up, and use her spells to find other ways to feed your dragons.

Their way only gives them a short term gain, feeds their beasts once, and costs them a magic user and whatever spells that day they needed to use to be sure they extracted the maximum amount of knowledge from said schmuck (if they could even be bothered to do that much).

They're worse than stupid, as @Crake pointed out, they're inefficient, which is a far graver sin.

I bet they don't even use the soul, just toss it out like barbarians.
They try to hire them first, their rule is that anyone who agree to join them get a clean slate, those they feed to the Drakes, are either enemies they fail to turn, or mages who broke the rules after joining.
Crafted items are not valid as sacrifices for the Old Gods, so I see no reason why they would be for Tiamat.

Unless...

Is Tiamat secretly poor? Is her jewelry from the thrift store? Was her vacation in the Plane of Beaches a lie?
This is not sacrifice to Tiamat, this is food for her Drakes, the Drakes just need magic to function, and so any magic will do.

Although Tiamat probably do take crafted item sacrifices, just her rates for those are probably horrendous, but she's the goddess of greed, she's never seen a valuable she didn't like.

If feeding the Drakes is sacrifice to Tiamat, they might have better rates for unique stuff, but she's the goddess of greed, there exist no even vaguely valuable stuff that she don't want, so she has rates for all kinds of stuff, the only reason they can't just feed her Drakes obscene amounts of precious metals, is that the Drakes aren't built with a compatible coin slot for that.

Tiamat is probably one of if not the easiest god to make sacrifices to, to offset this she has some of the worst rates, but she's the goddess of greed, if it can be considered to be worth something, she want it.
I wouldn't say so.

He is withholding something from her, basic enough that she's willing to pay in wishcraft for it.
Seems like a pretty normal hostage/abductor relation, which is not a good one?
I read it more that she has special wants, that he wont fulfil without payment.

She's a genie to start with, they don't really have basic needs, they don't need to eat, I don't think they need to sleep, they have a fair deal of magic, that are rather good at materialisation, so most other basic needs such as clothes she can probably just make, I'm guessing she's asking for books to read, or more likely since Galzerai wont grant it for just minor payment, such as use of her lesser abilities, she's asking for something like a personal bard to entertain her.
 
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I have another challenge proposal. This time with a twist.

Starting Timeline:
1) You are inserted into one of either ASWaH!Prime timeline at the start date of the first update. Nothing is guaranteed, the timeline isn't sacrosanct and the smallest action can have incredible repercussions down the road.
2) You are inserted shortly after Viserys has annexed most of the major political entities west of the Bone Mountains aside from Yi Ti which he is still subtly influencing, or else rendered them Protectorates in all but name. I would say this is a few short years before thing get incredibly hairy for the main cast, but they are certainly on a very long winning streak, but consequently they are full up on all kinds of new allies you've never seen before and your conditional bargaining position is even less than some of the other challenges presented here, depending on your approach.
3) You are inserted into canon at the Quest's start date. Magic has awakened earlier than usual. Things are very different, but as @Goldfish states, the Planes are mostly functional, Asmodeus isn't currently too busy WINNING to care what you think, and there is no Void. All apocalypses in the grand scheme of things, even ones that swallow entire planets, aren't completely guaranteed to ruin your fun.

Starting Locations:
1) You can start in any major population center, but you just did something to severely shake things up and accumulate memories of what it was over the course of the next week. By that point trouble will have likely caught up with you unless you were incredibly careful as a matter of course.
2) You start scattered throughout Planetos. More on this later. But you accrue Double the value of any Benefits mentioned later on individually.
3) You start scattered throughout the Planes, but accrue triple the Benefits mentioned later on.

Starting Conceit:
1) You can pick eleven other people from the thread to accompany you into your challenge. However, they acquire all of the same Benefits that you yourself do. Alternatively, you can pick some people from other boards if you happen to find them more trustworthy or just easier to get along with.
2) You can select eleven other characters from popular fiction to accompany you into your challenge, though without any of their base abilities if they should possess them, they will in essence remain themselves. They can be Composite type characters, having the parts which make them worldly, experienced or just the most useful version of themselves to you at that time, or they can be drawn from a particular point in their personal journey. They are aware of the stakes of the challenge and have provisionally accepted your invitation to work together, but they are their own person and their motives will inform on their decisions taken once the challenge begins. This excludes ASWaH!Prime characters. As above, they share every Benefit that you yourself do, at the cost of 1/2th effectiveness.
3) You can select a mix of the two above, people from real life to stack the deck if you're an extrovert who has a better read on family or friends, or even ASWaH!Prime characters. As above, they share all Benefits you yourself do, at the cost of 1/3rd effectiveness.

Starting Benefits
1) You gain one level up to 20 every year, and it is additive with your current XP, not accumulative up to the cap. So your progress isn't reset in the middle of some heavy adventuring, nor are you given disincentive either way to accumulate more XP. This rate can be doubled or even tripled depending on your previous selections, or alternatively halved or cut down to a third of the stated Benefit.
2) You can choose whatever template or starting race you feel like, but also have to pay off the level adjustment out of the above Benefit. You can only choose one, however, you can select a Race and a Template if you chose Location 3 and Conceit 3.
2.1) Feat, race and class selection is fairly generous for first level. Wedded to history? Grab it now if you want it, because you can't get it later. Rare race or template? Same deal, barring what you could reasonably acquire in-challenge due to your own efforts.
2.2) Elite Array is yes if you select condition #1 for Locations. 32 Point Buy for Condition #2. 36 Point Buy if you opt for Condition #3.
3) You can only qualify for PrCs if you meet the requisites, but there is absolutely nothing stopping you from retraining at any point you gain the first Benefit, at least until Level 20. After which, you can only retrain "a sane" amount as would reasonably be believable, typically one retroactive decision a year, like swapping feats that aren't locked in due to pre-requisites of a class or which were granted because of a Wish or Miracle or similar circumstances, those being metaphysically "bonded" with you, or retraining a PRC, so long as you don't lose the prerequisites which allowed your entrance to the first level until you are ready to leave it.

Starting Challenges:
1) Asmodeus is "indisposed", Baator is currently in the middle of a Cold War, and Avernus has been taken for keeps by Tiamat. Many of the Archdukes are kept from maneuvering to take over due to having to keep the course of the Blood War from reversing, as Tiamat has co-opted considerable resources and metaphysically taken hold of the Plane, and is directing all of it towards her own goals. The center-point of your challenge will inevitably draw you into this plot-line whether you like it or not, though the degree to which it effects you depends on your starting Timeline.
2) Many Gods become aware of your presence and some subtle alterations to events fated to take place due to it. No more of an advantage than they might gain after you have made several moves in the board, but chances are you will get wrapped up in some kind of shenanigans due to this whether you like it or not. You are too interesting to ignore now.
3) A Negaverse Rift Opens! A "Counter Group" is inserted along with yours! They're all oddly familiar, oh wait, THEY'RE YOU! What madness will this entail? Find out, next time on Dragon Ball Z!
Okay, so I'm going to pick something that isn't a Dragon or high-CR race, just for variety.
I mean, it's still high-powered (endless spell slots + access to Miracle, at level 10) but it has to cast a cantrip every other round, so it remains quite defeatable in battle. It would probably even lose to those Dragons! But it's so much more versatile out of combat... Rolling with this :
  • Timeline doesn't matter that much to me - Timeline 2 is clearly the best, but considering the race I picked I'll probably not be wholeheartedly accepted (especially if they try to divine me, fail to divine RoB, and think I'm some sort of unwitting pawn for the Elder Brain). So that leaves Timeline 1 or 3. In both cases I have about a decade until the Long Night, which is absolutely fine.
  • I really wish I could pick starting location 1, but I need to start with Int 17 if I don't want to rely on somehow finding a +2 Int item before level 10 on Planetos, while I may not be able to craft. Location 2 it is, then.
    • Being in a random place on Planetos (even if it isn't immediately lethal) is a problem. I'll be taking ranks in Survival, and will start with cross-class social (+ racial bonuses) and stealth skills instead of Knowledge. Retraining may occur later.
  • Starting Conceit : The Tiamat Plotline. This is the plotline that seems most likely to wait for a few years before it kicks off if I precommit to involving myself once I hit level 10 (so probably in 4 years, assuming I gain a single level through XP as I struggle not to die).
  • Build : Changeling Wizard 5 (Illusionist - no evocation or necromancy - with Gnome racial sublevel, Shadow Shaper and School Mastery ACFs) / Shadowcraft Mage 3 / Recaster 5 / Shadowcraft Mage +1 / Mindbender 1 / Shadowcraft Mage +1 / Master Specialist 4
    • Feats : Racial Emulation, 2 Flaws, Heighten Spell and Spell Focus (illusion), Sanctum Spell at level 3, Item Familiar at level 6, Residual Magic at level 9, Darkstalker at level 12 (I have Hide in Plain Sight after all), Mindsight at level 15, Skill Focus (Spellcraft) at 17, Heighten Spell (I'll Dark Chaos Shuffle the old one into Wedded to History by casting the spells myself) at 18, and Greater Spell Focus (Illusion) at 19.
    • Stats : Str 10, Dex 10, Con 12, Int 18, Wis 12, Cha 12
  • EDIT : At level 10 I can use the Shadowcraft mage shadow illusion ability to replicate any spell of 9th level or lower (thanks to Heighten Spell, Sanctum Spell and Residual Magic) by casting a heightened Silent Image twice in a row (from a very low-level slot, and then from a cantrip slot but counting as if heightened to 9th+1 thanks to Residual Magic). Then Recaster adds Miracle to my spell list, letting me replicate it. Miracle lets me replicate Mordenkainen's Lucubration, which lets me regain more spell lots than it took to cast the spell. Bam, infinite spells, 50 of which can be shadow Miracles if cast every other round.
    • Is this enough power to win every fight and defeat Tiamat? Probably not, unless I can somehow summon an infinite number of Celestials to defeat her infinite number of Demons (AFAIK, impossible). Is this enough power to make my personal life incredibly convenient? Well, yes, that's the point.
At the beginning, I'll basically be a hobo with minor skills. Once I reach civilisation I'll probably do well enough - Changeling racial ability is good for avoiding the problems of relying on low-level magic to make enough money to eat (monetise Prestigiditation or Mending, etc). Reaching civilisation could be difficult, especially if I end up in the Dothraki sea or something, but again I have good spell DCs, good ability to fit in (physically at least - even if I stick to Gnome forms, the difference between "ugly, tall gnome" and "short woman" isn't that huge and I have a +10 racial Disguise bonus + I avoid some of the base Disguise penalties) and magic for emergencies. Illusions don't even allow a save if you don't touch them, and the people in base Planetos aren't exactly on the lookout for low-level illusionists (many don't even believe in magic at quest start). Once I start gaining levels, these problems vanish rather fast (even level 2 spells, available from year 2, are a huge step up).

Another potential issue may be getting spells for my spellbook once I enter PrCs. Sure I'll have Shadowcraft Mage to minimise this problem, but I will almost certainly have to adventure to learn more spells, or to earn the money for spell research. This stops being an issue after level 10 of course.

So, yeah, a big gamble here. The first year will probably be difficult, but after that things get exponentially easier.
This build isn't perfect. Ideally I'd have done all that while being a Dragon (possible with Stoneblessed!) but I was trying to pick a LA+0 choice here.
 
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Inserted tally
Adhoc vote count started by Goldfish on Jan 23, 2020 at 4:57 AM, finished with 53 posts and 13 votes.

  • [X] Incline your head slightly, letting none of your surprise show. "Fairly said, I would not wish to betray the confidence of even my own hostages." Though you value your given word equally as much, even somewhat for pride's sake, that you have seen fit to adhere to it as much as possible, you know he likely feels little of the sympathy for the Princess that you felt for your cousin Stannis at the time. "I will see to it that the Emir knows your mind on this matter."
    -[X] "Elder Cousin, this discussion has proven not only productive, but insightful. I would not wish to tarry more than necessary, but should you wish to engage in further dialogue, be it with fruitful exchanges in mind or merely slaking one's curiosity, know I too hold you in high esteem for the courtesy shown, and would in similar regard grant you passage to my realm at a time of your choosing. Further, I offer you the opportunity to open an Embassy in Sorcerer's Deep."
    -[X] Depart for the Kelasi Emirate.
 
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