We already know he is there for convenience sake, not because he is ill or broke. This is not a hardship case, so there's no reason for him to be there, let's face it. Maybe your DH could urge him to look in earnest for a place of his own, and actually help him. Sounds like he needs a shove in the right direction. It would help to give him a deadline, too, like 3 months or so. Tell him the house is too crowded, and of course, he and his dogs would be more comfortable in his own place. It's not right for him to come in and take over the house - it's not his house, after all. You don't need creativity to give him the message, your DH needs to tell him directly because he's gotten too comfy, and why should he want to move given those circumstances! And you, if you have not already, should tell your DH your sanity depends on it! You could make it one of those "either he goes or I go" sort of deals.