The Powers That Be:
I think we can start brainstorming the story we want to tell. I think for the kind of story we want to tell, a small cast of player characters (protagonists) might be good.
I completely agree that a small, manageable cast of characters is preferable in this case.
Say maybe a maximum of four to start? And we can adjust from there?
As far as the sort of story we want to tell. Here are a few broad strokes I will throw out for the sake of discussion.
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Knighthood
Classic adventure material. The characters are all arms bearing men of some sort.
Perhaps they are, or were, all squired to the same Knight?
Perhaps they have aspirations of joining the Order of the Golden Fleece?
Perhaps they are what is left after saber rattling or military posturing has drawn off the bulk of the local forces?
This story may involve concepts of chivalry vs practicality, the role of armed enforcers in the feudal system, or the "disconnect" between the orders or whims of the nobility and the situation on the ground.
Despite all being somehow involved in an arms bearing trade, their personal experience, campaigns, backgrounds, superiors or cultures could provide enough diversity to prevent gross duplication.
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Courtiers
Knee deep in machiavellian intrigues, the characters are based in
Bruges, and have responsibilities to their patrons, their families and the Court.
Perhaps they are trusted advisors? Related to a key figure in the ongoing situation? Or party to a dangerous shared secret after.
This sort of story would involve a lot of talking, a lot of NPC's and more of a "slow burn" atmosphere. That's not to say there could not be some foot chases, some illicit meetings, maybe a knife in the dark, but this is more of a cerebral story.
Exploring the burden of privilege, the ties that bind the characters to their families, and the life of the nobility might all be themes here. As would faith, the barrier between the Church and the state, and witnessing how government "really" works. The sausage being made...so to speak.
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Barony
"Small scale" action with limited resources.
There may be big things going on in the Capitol, but they are far removed from your daily concerns. The characters are all capable subjects of the local Baron, brought together to handle affairs in the Manor and the local countryside.
This is the sort of story where every significant NPC in the Manor could be known by name, as could the significant tradesman in the community. The sort of story where a local map could be made and utilized for the vast majority of the story.
This would also allow for a more diverse skill set in the characters in exchange for a smaller locality. They are literally just a collection of capable individuals that the Baron trusts to handle things on his behalf.
Manor house drama instead of court intrigue.
This sort of story would allow the more "common" sorts to shine, and to perhaps even advance in station depending on how they play their cards.
But it is also a "down in the mud" sort of view. You are dealing with the peasantry directly, the front line, so to speak.
As I said, broad strokes, and just an example of how we might go about narrowing down the story to a common theme instead of having a bunch of disparate characters pursuing their own goals.
Conversation material.