I can see any number of endings. I'm pretty sure that the darkest paths will lead you to a bad end sooner or later - though I don't know what that looks like. On just about every path though MC is headed back toward being poor. He's very rich but he's burning through money at a rapid pace and not investing in anything that is likely to make much money. Brick and mortar book stores don't make money anymore, and I know a guy who owns two resteraunts and a micro-brewery. He works 70-80 hours a week, owns a small one-bedroom house and drives a beat up 20-year-old pickup. So it's not that he makes zero money but definitely not wealthy. His other spending, so far, is straight up charity, so I can easily see him becoming poor again. But I could see a scene where he's working at the convenience store again and one of the girls walks in and if he helped her and she's successful now she goes up to him and says - you deserve better than this and helps him in return or if he manipulated and abused her, just shakes her head and walks back out.