It honestly sounds like you're being taken advantage of. I'm sure it's hard to separate any feelings of fondness you have for him from the idea that he's taking you for a ride (whether consciously or not), but he certainly is. You aren't doing anything wrong, but you are certainly enabling his behavior every time you make a concession. Maybe he isn't a horrible person, we all get down on our luck, but he certainly seems to be a selfish person.

Might be time to focus on you and let him, like the adult he is, work out his own financial issues. That's your call, of course. But your posts make it sound like you're ready to get out (maybe not break up, but separate your finances). It's up to him from there to get his ducks in a row; not up to you to wait and continue playing the patient and supportive partner when resources are finite. Tough situation all the way around. Best wishes.