I want a perfect run in Westeros. The main issues with Westeros won't be the conquest: they'll be in the postwar administration and reforms.
We need a strong army and bureaucracy ready to roll out and over the barbarian hinterlands. This isn't a fight we can win by waltzing in and killing anyone who sticks out on the Evil-O-Meter!
 
Mind you that I low-balled our forces there. Volantis alone should have 50,000+ soldiers for us to absorb into the Legion.
 
@Azel Volantis should have the Banners and any local mercenary/semi-professional border guard free to absorb into the Legions, which should account for that much, yeah. Maybe more technically if you go for pure recruits from former slaves, easily. There's some numbers that can be balanced especially with agricultural reform.

Braavos and Pentos should have plenty of mercenaries that we can entice to join the Legion, as well as the martially inclined youth based groups in the former who make up a lot of Braavos' military during times of war, with the added benefit of plenty of nobles forming that group who know their letters--ready made officers.

I also believe out of the Disputed Lands we can raise one Legion from already-professional forces per Free City, in addition to our 1st Legion.

So with all of those put together, I expect something like 10 Legions as a conservative estimate on short notice, with 12 being possible if we step up mobilization a notch or two. Definitely 12 Legions if we postpone invasion another month or so, though they'll still have some kinks to work out, they should be fairly organized and disciplined since we're mainly recruiting more seasoned men.
 
The Westerosi Problem

Actual 'threats' to us: a little unclear since we have no real up to date intelligence besides interludes, but from rumors and inference we can nail down some targets. The most obvious and proactive enemy are the Lannisters, who have embraced magic as well as their already considerable influence and dangerous levels of competence. There's the Crown, Cersi (who is confirmed to at least have access to magic items) and Robert (who we know nothing about, but is probably in better shape than in canon), but it's fair to assume that they'll ultimately pose little danger. Of the Regions, Vale nobles may be making deals with devils (Lysa and the Corbrays) which is ironic and sad, but Yohn should be doing good work there. The Reach is a wildcard, but the Fey are heavily involved if not directly antagonistic, something we'll need to handle. The Maesters are of course being the magic-hating bitches that they are, and presumably have a significant arsenal of artifacts and knowledge at their disposal as well as signifigant influence over the average westerosi lord. There's the Faith ... which is going to a long, aggravating, and probably dangerous issue. The leverage we have here is that they're not all united in purpose - of the Champions of the Seven themselves, we could subvert at least 2 (Brienne and the Maiden's) and Bloodraven is almost certainly fermenting a schism. Then there are the Others, which require no explanation from me. Individual houses may have their own gimmicks (Boltons, Daynes, and apparently the Westerlings now) but they won't be necessarily hostile or a genuine threat comparatively.

None of these things would make a Conquest impossible ... but as several other people have pointed out, the real issue will be enforcing our will on a continent and prevent chaos from breaking out. I have no doubt dozens of monsters and factions will see this as their time to shine, and I hope we'll have purged the Deep Ones before we do this as they will almost certainly capitalize to everyone's detriment.
 
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@Azel Volantis should have the Banners and any local mercenary/semi-professional border guard free to absorb into the Legions, which should account for that much, yeah. Maybe more technically if you go for pure recruits from former slaves, easily. There's some numbers that can be balanced especially with agricultural reform.

Braavos and Pentos should have plenty of mercenaries that we can entice to join the Legion, as well as the martially inclined youth based groups in the former who make up a lot of Braavos' military during times of war, with the added benefit of plenty of nobles forming that group who know their letters--ready made officers.

I also believe out of the Disputed Lands we can raise one Legion from already-professional forces per Free City, in addition to our 1st Legion.

So with all of those put together, I expect something like 10 Legions as a conservative estimate on short notice, with 12 being possible if we step up mobilization a notch or two. Definitely 12 Legions if we postpone invasion another month or so, though they'll still have some kinks to work out, they should be fairly organized and disciplined since we're mainly recruiting more seasoned men.
I'm counting on enough recruits for 2 more legions this month alone.

We still have 10,000 "border guards and militias" on our nominal payroll there. Which is most likely an overblown number since a lot of that money is likely going towards corrupt officials. Add to that raw recruits out of a slave population of 2.5 million people. Add to that the former household troops of various magisters who are headed for the gallows and we should easily scrounge up 15,000 recruits in total, which would be enough to fill out the 2nd and 3rd Legion.

To that, we can add the survivors of the Lyseni invasion, more recruits from their part of the Disputed Lands, whatever forces we can snatch from Myr and yet again more recruits from their lands.

Our military budget will skyrocket, but so will our forces.

I would expect, from Lys and Myr combined, 2 Legions ready to deploy from sellswords and other (semi-)professional fighters and another 4 if we do some recruiting efforts.

So I'm spitballing it at 9 Legions from the Three Daughters alone. Given Volantis size and recent recruitment acitivites, we can probably snatch 4 Legions in a ready state and 10 or more in recruits.

Tolos and Mantarys should each have enough warriors ready to form one Legion each, which sadly has to stay in the east.

So I'm thinking 13 Legions definitely and up to 25 if we wait a bit and pilfer soldiers from mercenaries to balance out the less well trained recruits.
 
Dont forget to factor in casualties in to your calculations guys.

Our conquests will not be bloodless. Especiallysince volantis and myr are expecting it.
 
I'm counting on enough recruits for 2 more legions this month alone.

We still have 10,000 "border guards and militias" on our nominal payroll there. Which is most likely an overblown number since a lot of that money is likely going towards corrupt officials. Add to that raw recruits out of a slave population of 2.5 million people. Add to that the former household troops of various magisters who are headed for the gallows and we should easily scrounge up 15,000 recruits in total, which would be enough to fill out the 2nd and 3rd Legion.

To that, we can add the survivors of the Lyseni invasion, more recruits from their part of the Disputed Lands, whatever forces we can snatch from Myr and yet again more recruits from their lands.

Our military budget will skyrocket, but so will our forces.

I would expect, from Lys and Myr combined, 2 Legions ready to deploy from sellswords and other (semi-)professional fighters and another 4 if we do some recruiting efforts.

So I'm spitballing it at 9 Legions from the Three Daughters alone. Given Volantis size and recent recruitment acitivites, we can probably snatch 4 Legions in a ready state and 10 or more in recruits.

Tolos and Mantarys should each have enough warriors ready to form one Legion each, which sadly has to stay in the east.

So I'm thinking 13 Legions definitely and up to 25 if we wait a bit and pilfer soldiers from mercenaries to balance out the less well trained recruits.
By the way, shouldn't we be poking at the Xorn and Shaitan for more iron?
 
Dont forget to factor in casualties in to your calculations guys.

Our conquests will not be bloodless. Especiallysince volantis and myr are expecting it.
I'm actually just waiting for the Planar Conference results to get in to make the Myrish Glassmaker Guild an offer they will most likely consider very interesting. Likewise, Lys itself will fall by coup and their invasion force is earmarked for Rhango to take apart as he sees fit.

No big losses there, since we won't force large engagements.

And Volantis will fold peacefully, thanks to our little deal with Zherys.
 
When are we making Bronn a lord?
Last time I remember this coming up I argued stringing him along is the smart move. He should get bigger rewards only when he forces our hand by accomplishing something very impressive.

Regarding Westeros I agree with the general rumblings of impatience. At the very least I'd like more focus on Westerosi events now. We've been inching closer to conquest and now we're pretty close indeed.

We should decide on a rough timetable (something along the lines of "military invasion in six months") and be gradually paving the way from next month on in terms of politics and intrigue.
Our conquests will not be bloodless. Especiallysince volantis and myr are expecting it.
We've got Volantis well in hand. I don't expect Legion casualties there.
 
Personally, I care very little for Westeros and would like to put it off as long as logically possible.

I like Essos fluff more.
I like ancient civilisations, I like us having a clear enemy in face of "slavery" here, I like facing a multitude of disorganised opponents, instead of 1 organised (however poor).

I like us playing "The Big Game" now and making very big waves in planar perspectives.

I like dealing with loot-promising and headache-not-inducing stuff, like raiding ancient temples, killing off undead hordes at dothraki sea, looting people from beyond the Wall, or getting descendants of those undead spirits to their birthright.

Tldr: Westeros promises a significant change in pacing and in-quest activities, and I'm uncomfortable with some of such changes, if only because I'm bad at intrigues and because I don't like Westeros fluff much :/

Bottom line?
I'm okay with dealing with Westeros, once we have have completed:
A) Red Dragon Orb fetchquest
B) Tiamat forces eradication and Meraxes avatar-raising fetchquest
C) Preferably once we have dealth with Slaver's Bay and Pentos. Aaaand maybe Warlocks.
*) Bonus points for killing off Black Goat.
 
And how many legions do you guys think we will need? I personally dont really see the need for more than 10
Don't forget that we need to leave some behind as garrisons.

I would leave two Legions in the Stepstones, Disputed Lands and Lys, both as a strategic reserve and as garrison.
Myr will need a full Legion on it's own, due to controlling a lot of territory.
For Volantis... I think 3 Legions should cut it.
Probably another Legion for the Basilisk Isles, if Salladhor is making good progress there.

So we need 7 Legions already just as our defense.
 
Remember people: we will lose time administering Essos. Setting up our bureaucracy, hiring and training them, doing our own little slavery "denazification" in Pentos, Lys and Myr...

Now I expect a lot of this lost time to be timeskips, right @DragonParadox? Or will we have 20 chapters of this after each city?
I would be fine with that actually, as long as it isn't always the same kind of problems. We can mostly offs teen what will become our larger policies and keep dealing with weird local issues like those firemen in Tyrosh.

Still, I expect we will be conquering Westeros in Mai 2019, and that we will still be administering it and fixing local issues in next September.

Once we have both empires fully set up... Probably more focus on extraplanar stuff, and striking blows against our true enemies (Others, Illithid...). Or maybe the quest will just end :'(
 
Which reminds me of something else...

@Goldfish, if the Wight research pans out, I would like to reserve up to 10 wights for military projects. My personal crafting backlog is tremendous and with the windfall of our Adamantine turtles, I'm finally secure enough on the financial front to push for it.

I will also need a shit-ton of alchemical ammunitions.
 
Plus many of the Volantene soldier's allegiance go to the High Speaker. He was the one who supported them since the very beginning. Those still alive at least.
 
I like ancient civilisations, I like us having a clear enemy in face of "slavery" here, I like facing a multitude of disorganised opponents, instead of 1 organised (however poor).

I like us playing "The Big Game" now and making very big waves in planar perspectives.

I like dealing with loot-promising and headache-not-inducing stuff, like raiding ancient temples, killing off undead hordes at dothraki sea, looting people from beyond the Wall, or getting descendants of those undead spirits to their birthright.

Tldr: Westeros promises a significant change in pacing and in-quest activities, and I'm uncomfortable with some of such changes, if only because I'm bad at intrigues and because I don't like Westeros fluff much :/
I like all of that stuff too. The quest would be much less unique without it. But I also like variety and I have a fondness for canon ASoIaF which focuses primarily on Westeros.

I'm not convinced Westeros will be such a big change in pacing and activities. Many ways DP could handle it.
Now I expect a lot of this lost time to be timeskips, right @DragonParadox? Or will we have 20 chapters of this after each city?
Timeskips would require some serious changes to quest structure. I'm wary because I think ASwaH is in a good state right now.
 
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