This is iteration nine million of the same song and dance. He feels entitled and contemptuous right up until he gets some unavoidable consequence, and then he is sorry and feels bad. The minute things get better, he reverts right back to entitlement and contempt. At the time, he feels genuinely horrible and sad, and will do just about anything to "fix" the situation. But it never lasts. I'm worried about him, but as it turns out he didn't even check the shelter, which is four blocks from here, so if he's been sleeping rough it's because he hasn't exhausted all his resources. It's a little frustrating that he admits to using drugs but denies having a problem with drugs or alcohol (the reason he gave for not going to the local 12-step place, which is open very late, has meetings hourly on Sundays, and could maybe find him a place to crash). I'm just so tired of being lied to.
ETA: And, yes, you're absolutely right - the whole point of this exercise for him is to get his needs met, by whatever means possible. Right now, the path of least resistance has traditionally been making me feel bad for him and wearing me down. That's not working for him anymore, and he's like the rat that keeps pushing the button frantically although no treats are being dispensed.