Most relevant to this guy from what i'm seeing will be Desi, who is the 'Boss of Bosses' in Boston. He's the Boss of the Vargas Family and controls the underground in Boston. Basically nothing happens within the city criminally without his knowing or approval unless you want not so good trouble. He's been in power a little over a year now after his parents retired and has three younger siblings and a slew of family to help him keep things in order. Plus a hitman on the payroll he trusts. Legally he owns various restaurants, pubs, eateries, cafes... The like. And he has a 19 year old daughter; touch her and he has no issue shooting you. -insert evil grin- LOL. He's 36, so there can be lots of potential here. Though I would have to warn you, Desi is very traditional and family oriented so he'd not look favorably on your guy turning on his brother, which can always be some fun contention. He is a Reigner.
Bethanie is another, as she is the manager and bartender for The Merry Men, her uncle's bar in Dorchester District. A rough area and all. She is forward, a tad shameless and loves to mess around. She wear very little clothing while behind the bar and working the floor, it's likely something of a draw for patrons... lol. She is a definite bad girl type, with some morals... somewhere in there... She is an Intermediate.
Aran's an Acquiescent, a masseuse and an avid clubber.
Marek is also an Acquiescent, a student, family heavily and law enforcement and well to do in the city. Cute and adorable.
Norah is Nicholas' Helot, his favored one at that. She is chipper, happy, perfect poster child for Helots.