I really, really, like your plan. You'll be protected from his current irresponsibility, but you aren't closing the door. I don't know whether he has it in him to really address his issues, but you are giving him a chance. To me, that is a very generous action on your part, and I think he recognizes it. We don't know what he has in him, but as you said, who knows? You never would have expected him to be where he is today, maybe he can surprise you again!
