@reaperoa Thanks for the feedback–it’s good to see things through another’s eyes (and rethink accordingly!).
True enough, I’m certainly guilty of assuming that most, if not all, real gangsters were basically fairly nasty people (that said, I also believe they were, for the most part, a product of the time and place in which they lived; i.e. more or less conditioned to behave a certain way).
As for the college graduate background, this very almost didn’t make it in at all simply because it was such a rarity historically: before the 1920s, fewer than 1 percent of first-generation Italian-Americans even made it to high school. Most were forced into work (or petty crime, in the case of most wannabe gangsters) in their early-mid teens.
In the background for college grad I therefore tried to depict someone who started out just like everyone else around him (“a dumb bloodthirsty brute”, as you put it)–i.e. a product of the ghetto–but, when actually given the opportunity to change, he went and made something of himself and gained a real education. Of course the story then puts him right back where he started, in line with the overall theme of the game, but how you play him from that point on will, of course, be the player’s decision. Perhaps more than any of the other Backgrounds, the college grad does not really have the stats to be successful as “a dumb bloodthirsty brute”, and would likely not do very well if that’s how you chose to play that one. His particular strengths are, in fact, almost the complete opposite.
On your other main point (early interaction, or lack thereof), I agree entirely that I’ve spent far more time setting the plot than is usual in a typical ChoiceScript game. This was a concious decision on my part and is partly due to personal preference, but mostly because I wanted to immerse the reader in that time and place–i.e. the story–before they begin to play the actual game.
It might indeed have to be slimmed down in the final edit, though: if asked to describe my style in one word, it would likely be “verbose”. Others would probably put it less kindly. 
@JimD Thanks, Jim, that’s a really great suggestion. I was so wrapped up in providing the historical stuff to put everything into proper context, it never even occurred to me to make it part of the game itself. I kept it separate simply because only a minority are likely to be interested enough to read it (hehe) but in hindsight I agree that this could be done in-game (with an easy opt-out choice for the player at any point, so they don’t have to pursue it if they don’t want to). Yep, I like it a lot–thanks.
Your point about describing game mechanics in advance is well taken. I must admit, my design background is in deep strategy games–where players like to get their teeth into the nitty-gritty of the various elements–so writing those sections just came naturally . . . I’ll certainly have a rethink on the subject before the final release.