No stupid around here.... we are ready when we are ready.
Have you just told him to leave if that is what you want and allow him to deal with where he will go and what he will do? Its really not your decision once you have asked him to leave... and the less you know the better I think. I dont know just seems like you would have to spend alot of time and energy figuring out things that is not your problem if you ask him to go....
BUT are you sure your ready to end it... cuz you teach him its ok to keep doing this by allowing him back. I have been told to watch the actions for a year before making a committment.