Let me see if I got this right...the dude is UNEMPLOYED, living with some chick and her kids who gets FOOD STAMPS and WELFARE.
I'm not sure just how much more you're gonna be able to squeeze that turnip. Hell, jail time might be a step up for him. He'd still get free rent, the 3 squares a day might be better, free cable and no kids.
This guy sounds like a real winner. I would suspect that (given his apparent track record) this clown isn't smart enough to find a way to get paid any significant amount "under the table".