I like the pics for prisoners idea, but prisoners cannot have cash. They have commisary (or "books") which works like a debit account to buy the things that prisoners need. The family & friends of the prisoner put this money into the account. The inmate himself may have a job in the prison (like making wood plaques or building office furniture) but they get paid like 20 cents an hour and the money goes to restitution fees or commisary.
You'd have to market to the friends/family of inmates...
Oh! I just remembered that there is a company that creates personal ads for inmates, maybe you could talk to them.
http://www.meet-an-inmate.com/
Bookmarks