The answer is that it’d look much like Chapter 1 does now. Chapter 1, regardless of the background you picked, is really heavily linked to stuff about the Hellions, and the reason that the Street Gang Leader looks boring is that every path still starts off with a lot of Hellions business.
Personally, I think that too much focus on that, specifically, would dilute the game, and I think there should be less focus on the backgrounds rather than more. The thing is that all of the backgrounds dovetail into one trajectory: your path to becoming a mob boss.
Imagine the game focusing on your past as a College Graduate. Why the hell should other gangsters care about your motherfuckin’ diploma? People like Russo and Mangano, what they gonna care about is that you came back home knowin’ how to run a racket and keep dumbasses like Dino pointed in the right direction. Likewise, the Hellions are kinda small time and most of the people you ran with are now runnin’ bigger things. You’ve attracted the eye of the Ginellis, and by the end of Chapter 2, you’re the boss of Navy Street, even if you told Mangano to take a hike, even if you didn’t ask for the job. With that kind of status and income, why the hell are you wastin’ time with the Hellions, except maybe to use 'em as muscle on bigger stuff?
