When it comes to the free rent make sure you still have him sign a contract though where there is no doubt that he eventually start paying rent. Where it lays out month one is $0, month two is $0, then eventually month four is $500 or whatever. Because he could possibly try to say if you start to ask for rent after a few months that he thought you were providing him a free place to stay till he got on his feet. And you could say that will take a few months and he could say it'll take him a year or two. And then if you would ask him to leave once he has all his mail coming there you have to go through eviction, not allowed to just throw him out.
I watch a lot of The People's Court! 👩⚖️