okie girl, I remember getting confused, too, about money I had spent, and then I was also really mad, at him and at myself, so I wanted to get SOMETHING back for all my troubles.
My ex-husband (his dad) and I had helped him get a nice used Toyota Camry that he picked out---that car was so clean. He was supposed to pay both of us back for the car over time. Never saw a dime of it.
And then, finally, the car was so completely trashed out, inside and outside, and my ex had it towed to my neighborhood to store where we have a fenced in area for boats, etc.
I would look at that car, and cry. It was a metaphor for his life. So much promise, and then, completely wrecked.
Finally, he got the car, and got it going, and then sold it as is, got enough to pay for another car. I didn't spend any more money of my own on that car. We by then had learned the hard, hard way that either he was going to have to figure it out, or it wouldn't get figured out.
But I remember all of my emotions surrounding that car. We have to completely let go of the past, and our involvement and our anger, and disappointment and our Cinderella stories about "maybe this time, if I help with this, he will do THAT'.
Time for you and your husband. Let the system work. It will work just fine and his life will continue to move forward. Hang in there Okie Girl! Let it go, let it go, let it go.