Yeah it's a pretty depressing and challenging game. I beat this game with all the different scenarios. If you play long enough though, you can find a pretty simple formula to win:
- Find the nearest homeless shelter that is near a job board
- Take freelance jobs, putting the bulk of your earnings in a savings account and only keeping a little cash on hand for laundry and other things (otherwise it gets stolen at the homeless shelter)
- Spend all the rest of your time at the library studying until you can get a higher paying job
I'm not sure it's very realistic though because begging nets very little money and negative morale in the game, yet I think panhandlers can actually make quite a bit in real life in high traffic areas.