Can you call someone and find out the details of his getting out and know the details (he's got to be on some sort of "restraint" -- just paying someone to get him out, there are "rules" he has to follow) and I'd program a phone to call whomever if he breaks them on speed dial

Does not sound fun. Good idea to make sure all your friends know he's out (and the landlord, threaten the landlord with police troubles if he doesn't pay attention). Hope he decides it's not worth it to him and tires of his sick games.