Just miss a health check, or dont do enough days, or get low amounts of money for multiple weeks in a row. Any or all these things will earn you a place in the comunity service team (homeless content) though you may need to do them a couple of times if you have been good up till that point. Also, I think you need to have spoken to both your pimp, and the drug dealer guy that hangs out at the Belies place about the homeless punishment.
Other punishments are scripted, like an event with a cop and getting a day with their sister, but they are more story related.
I dont know if there are more punishments than the first round with the homless guy and the scripted ones I mentioned as when I play the mod I play it like the punishment broke the MC to just do what she is told. But, once you have had the punishment, if the MC enjoys herself, you can choose to continue to do comunity service whenever you want (it takes a while after the first time with the homless guy for the events to triger where you can choose to go back, but it will happen if you (MC) like getting treated that way).