Comparing the plans:

[] Expanding the Beachhead
-[] [Intrigue] Uproot Besim's Cache
--[] Add Free action to Uproot Besim's Cache

[] Plan First Besim, then the rest.
-[] [Intrigue] Uproot Besim's Cache
-[] [Stew] Just Look Up the Jurisdiction Part I
--[] Free Action

See, the problem here is that "Uproot Besim's Cache" is DC 27 and "Just Look Up the Jurisdiction" is DC 28. Our base die roll bonuses on those actions are 22 and 22, respectively.

So plan "FBttr" has us taking two plot-critical actions on which we have roughly a 50% and 40% chance of success, respectively. And where probable failure scenarios at best 'wasted time' and at worst 'we get caught red-handed and are somehow charged with trespassing or burglary and/or attacked by guards.'

I think that @TheShadowOfZama is right; we need to make sure to double down on certain actions to maximize our chances of accomplishing them, and/or take preparatory actions. Familiarizing ourselves with the nobles will probably ease either creating a jurisdiction, looking one up, or both; familiarizing ourselves with the local legal experts could do either.
 
Month 4 chronologically/Month (Turn) 3 in city: The itenerant labourers are in town and apparently, they are beefy. Mind telling us what Agueda knows of these lads, @huhYeahGoodPoint? Because a bunch of regular farmers shouldn't be a potential peril/opportunity.
I dunno. Thousands of physically robust guys coming into the city? Most of whom probably don't own land or property? Most of whom are willing to take some risks to get a stake and make a place in the world for themselves? Many of whom have experience on sea voyages or long stints of very hard labor to toughen themselves and harden their attitude toward danger?

They're going to be a force, even if usually an undirected and chaotic force. Expect a disproportionate number of brawls and riots when they're in town, for instance.
Simon_Jester's got the part of it. These guys are strong, need work, and don't have land or property. Many of them have formed into groups, either forged by wandering to farm together or by the sea voyages on the trade ships. There's certainly not going to be organization to them, and they're going to make the city rowdier while they're here. Tensions are going to be higher in the city; if the harvest is bad or the food doesn't come in on time it gets ugly, between the itinerant laborers wanting food and the city-dwellers wanting these wanderers and vagrants out of their city and the food going to the city-dwellers. This is aside from the risk of having literally thousands of workers pour in from the countryside, all possible vectors for disease, which is another risk entirely.

In other words, those months when the itinerant laborers, adventurers, and regular city-dwellers are all in the city. Tensions and tempers will be running high, without some good luck on your part.
Month 5 chronologically/Month (Turn) 4 in city: The labourers are starting to hop on trade ships which means that we might have an opportunity to get a) profit or b) informations on the ships transporting the chais.
Another important factor that I forgot to fully explain:

Those adventurers and mercenaries are coming and going with the trade ships. Right now, when the trade ships are in, you have hundreds of extra adventurers just scattered throughout the city; you're pretty sure that while the Port Authority's scam is quite lucrative for them, it's not going to beat out the profits from sticking with the merchants on their own adventure. That means that when those trade ships leave, they'll be taking a huge chunk of the adventurer and mercenary population with them.

Naturally, that will reduce tensions in the city, but it will also represent a drying-up of opportunities; while the current situation where the Port Authority can hire loads and loads of adventurers and mercenaries around the city doing odd jobs is certainly a huge addition in their favor, it's very easy to also hire your own respectable force. When those trade ships leave and take their mercenaries and adventurers with them, well, the Port Authority's mercenary company on permanent rotation and their also permanent adventurer support is going to be the strongest force remaining. Putting together a force to resist them becomes extremely difficult, not least of which because your mercenary hires are a lot easier to notice when there's only a few mercenaries left in town.
Month 10 chronologically/Month (Turn) 9 in city: A chance to confiscate the chais? Something along those lines perhaps?
And also the adventurers and mercenaries and itinerant laborers returning, yes. Fortunately, those workers will be going off to harvest, but those adventurers and mercenaries are going to be in town for a short while.
 
Tensions are going to be higher in the city; if the harvest is bad or the food doesn't come in on time it gets ugly, between the itinerant laborers wanting food and the city-dwellers wanting these wanderers and vagrants out of their city and the food going to the city-dwellers. This is aside from the risk of having literally thousands of workers pour in from the countryside, all possible vectors for disease, which is another risk entirely.
...I am just looking forward for Turn 3 Random Event Roll being a sub-10 on the d100.
Putting together a force to resist them becomes extremely difficult, not least of which because your mercenary hires are a lot easier to notice when there's only a few mercenaries left in town.
So in other words, Turn 4/Start of Turn 5 is going to be the moment where any sort of recruitment options are done and what forces we have would stick up like a sore thumb unless Agueda and shadowhobo do some Martial/Intrigue tricks on them? Also, just to check the power-level systems. What sort of gear do Adventurers have, as eclectic the whole group seems to be, that allows them to- by the reading- tango up with mercenary groups and win out?
And also the adventurers and mercenaries and itinerant laborers returning, yes.
Huh- That is neat. Would we be able to call in off-city reinforcements to confiscate the chais provided we win the court? Or would Agueda estimate that the court battle alone is enough to deter some of the armed resistance that our hired guns are able to win out?
 
So in other words, Turn 4/Start of Turn 5 is going to be the moment where any sort of recruitment options are done and what forces we have would stick up like a sore thumb unless Agueda and shadowhobo do some Martial/Intrigue tricks on them?
Recruitment DCs skyrocket Turns 5 and 6, yes. If your remaining forces are big and sticking around, it's going to pop up on people's radars and put them on notice.
What sort of gear do Adventurers have, as eclectic the whole group seems to be, that allows them to- by the reading- tango up with mercenary groups and win out?
Put simply, most mercenaries tend to hang around groups of Martial 16-20, whereas adventurers range from 16 - 25+. While the low-level adventurers are close but noticeably stronger than mercenaries, by the time you hit the mid-tier adventurers not even the best mercenaries can keep up. Their equipment starts out as worse than mercenary equipment, but mid-tier adventurer gear is usually a little better and top-tier adventurers gets stupidly powerful gear.
Would we be able to call in off-city reinforcements to confiscate the chais provided we win the court?
Depends. Who are they loyal to, and why would they help?
Or would Agueda estimate that the court battle alone is enough to deter some of the armed resistance that our hired guns are able to win out?
The court battle - and importantly, winning the court battle - would likely signal "this guy's on his way out and his enemies are about to take him down". It will probably deter some armed resistance, and inspire desperate resistance elsewhere.

On another note, let's close voting at .
 
Put simply, most mercenaries tend to hang around groups of Martial 16-20, whereas adventurers range from 16 - 25+. While the low-level adventurers are close but noticeably stronger than mercenaries, by the time you hit the mid-tier adventurers not even the best mercenaries can keep up. Their equipment starts out as worse than mercenary equipment, but mid-tier adventurer gear is usually a little better and top-tier adventurers gets stupidly powerful gear.
If your remaining forces are big and sticking around, it's going to pop up on people's radars and put them on notice.
Hrm, this does mean that going for both quantity and quality, we'd be noticed halfway through our mission but then again, by Turn 5, we should be out in the open pressing the Court Case.

Alright then:
[X] Expanding the Beachhead
 
BREWING SUSPICION MONTH 2 ROLL CALL
Expanding the Beachhead wins, 7-2.

Roll me 8d100s.

FIRE: DC: N/A. The higher the number, the larger the fire.
MARTIAL: DC: 10. BASE STAT: 16. Cost: 3 Budget.
DIPLOMACY: DC: 20. BASE STAT: 17. Cost: 4 Budget.
INTRIGUE: DC: 27. BASE STAT: 22+3. Cost: 0 Budget.
LEARNING: DC: 25. BASE STAT: 20. Cost: 0 Budget.
STEWARDSHIP: DC: 22. BASE STAT: 22. Cost: 2 Budget.
PIETY: DC: 23. BASE STAT: 20. Cost: 1 Budget.

Total Income: 0 Budget.
Total Expenditures: 9 Budget.
Net Loss: 9 Budget.
 
Why are you (and lots of other people) use martial as combat? Thats two different stats! Not interchangable! Good general does not equal good fighter, and best fighter in the word can not know what command is like!
The original CK-2 style quest from 5 years ago by Gauis Marius over on SB, did combine Martial as Combat so continuing the tradition?
 
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