I'm not sure about the perfect timing - I'm a programmer, not a game designer. It's kind of hard to get into debt anyway if you don't try very hard to do so on purpose. I mean, a few minutes of working the streets, combined with the traits you earn doing so, and your money won't ever drop below a thousand or so. I think to get into the debtor's prison the ordinary way is not easy to achieve after the first minutes of playing, and the bandit camp can only be reached far later. But on the other hand, it's okay not to put each and every possibility into easy reach all the time.