I beat it - my favorite part came from the first time I got a job, and realized that given my spending needs I was never going to be able to live on the pay the job was giving me, and I'd have to resort to robbing again.. This seems like a realistic way to drive home the feeling of being trapped you might experience as a formerly incarcerated person.. The dynamic of rehab being an important part of breaking the cycle, while also being very expensive and therefore requiring crime in order to achieve is also a good example of the way the gameplay rules reinforce a theme.
So some really powerful messaging built into the game rules in a way that is subtle and does not stand out as moralizing. Good stuff.