Well, seems the family didn't want him moving back in with them, so sure, it sounded like a good idea that he move in with you.
I think you are making this much more difficult that it should be, just sit him down and lay out the deal. I still think till November is too long, if you are already waffling now, by then, with more sob stories you will never get him out. Quick and decisive seems to be a better approach to me.
Good luck