Very tough decision indeed. I'm in a similar boat as well, it's my older brother, though. 3 months? Nope, going on 3 years. I pay rent, he doesn't, I have a full time job, he works when he wants. He makes damned good money when he does, but it gets pissed away and I end up with a stack of "our" bills. IIRC, he said he had $500 to his name.
I'm to blame as well, I don't tally up all the expenses, nor do I tell him. I just pay them. What comes around goes around.
To tell you the truth, it only bothers me sometimes, and then I get over it. All I have to do is remind myself that this is my brother, and there isn't any amount of money that could ever come between us, period. Really, after all, the core charge for his alternator did get credited back to my account.
This is a bit harder for me swallow. The family (he has 3 older brothers, mother, father, I'm the youngest) beats on me to pass the message that he needs to be gainfully employed again, and resume a normal, responsible life. I get sick of that. I don't want to be the bad guy.
He'll get back on his feet again, I'm sure. Only then, I may drop the bomb on the financial damage. Or, I'll wrap it up, and put it under the Christmas tree, or in a birthday card with no UOI.
When it comes to my family, I can never do as much for them, as they do for me.
I hope you get it all sorted out.
