I'm thinking about Paolo more as a bit of a rake, someone who likes to flow between the classes in his effort to hear the stories and songs that rise out of love affairs and intrigues.
I see him as something of an enabler of mundane relations for the covenant, able to engage on behalf of the covenant with low-born, mercantile, or noble groups. He could function as a "face" so to speak but I don't see him as a leader per se. He's too focused on music and playing for an audience.
Perhaps I'm being too heavily influenced by the minstrel in the Witcher series. Paolo is a bit like Dandelion but not as frivolous or shallow, perhaps more politically astute, more driven by art (though Dandelion is pretty committed to his music).
The Gentleman idea was initially driven by the idea that Paolo can move between classes fairly easily, but that could also be driven by the music emphasis and a public role as troubador or courtly player.
If I went with something like Black Sheep and Social Contacts, that might support that background a bit better without the constraint of Gentleman.
I can also see him being used as something of a pawn/rook by Elymas to further his schemes, and even if he recognized he, he likely would enjoy the challenge/intrigue/fodder for a good song.
Better to keep him out of low-lifes, I plan to make my Bonisagus have that as his focus, being born to low-life himself.
Plus, keeping your character from engaging with them, means he can keep his hands 'clean'.
So we have as sort of roles (correct me if I am wrong)
Pantelli: A mason who is the excuse for the covenant mundanely and is a craftsman and terram mage.
Elymas: Probably took a hand in organising the covenant. Specialised in mentem, and schemes, and manipulation. Gentle gift and skills allow for him to scheme with the mundanes.
Thymos: Is a vim specialist and warder, who also appears to have a demon problem
Paulus: A musician, performer and gentle gifted magus who can work subtle magic on the mundanes and charm them in person.
Gilbert: a bonisagus who moves in criminal circles.
Please correct any mistakes here, but I think it will help us not step on each other's toes if we have a brief idea of where we are interested.
So, in my gaming experience, if you are facing trouble a party wants to be able to:
Investigate
Schmooze
Intimidate
Kick shit
Understand mystic things
Know things
Sneak
Know people
Escape from places
Get into places they should not be
Can we cover those sorts of jobs as a group? I know it is a very meta perspective, but I have been in ars games where sessions crashed into a halt because we did not have the phenomenal cosmic power needed for the issue at hand and then we beat our heads against an issue.
I don't think it's important to cover all of those. Part of the fun, for me, is to be in situations where there's no one clear way to resolve them, and to become creative
We cover some of them with our Magi, we can cover some with companions, but we don't have to cover all of them.
I agree, you don't need them all. In fact, fun play is often having to cleverly step around a lack with what you can do. But if everyone is unable to do something it can be a stumbling block to games in my experience.
We seem to be able to talk to normal people which is great as that has been a sticking point in too many games of ars magica I have played where a scenario crashed and burned because no one could engage with any npcs helpfully, and so the information we needed to have a good time and the rp we could have with the environments were all shut off.
Mostly, I wondered if we had people who could investigate since I think we can at least half cover most of the rest with inventiveness, which is as you say, fun.
Paolo is a bit like Dandelion but not as frivolous or shallow, perhaps more politically astute, more driven by art (though Dandelion is pretty committed to his music).