I don't know if I just found a really good strat or if the game is just a bit too easy, but I won in about 10-15 days.
I agree with WitheredTulip, more dangerous clients should pay more, along with being more likely to be forceful (if they aren't already, it's hard to tell). Being caught stealing making future checks harder (although not necessarily extremely harsh) is also a good idea.
Stealing is currently still too powerful. With about 20 Wit and Power it's possible to repeatedly steal from low-level clients like students and tourists, racking up tens of thousands, and reliably pushing them off when caught. I would suggest a relatively strong stacking debuff on repeated steal attempts. I believe this can allow high wit to still be well rewarded, but make it much less OP.
Still enjoyed the game, keep it up.