Amy, as the others have said, it wouldn't be right for anybody to tell you what to do. I can tell you what line we finally drew - which is, we love you, we will speak with you (although we haven't spoken in two weeks), and we will support you emotionally, but we will not give you any money.
Now, to be clear, in our AS' case, sometimes we transgress that in that we have to pay for co-pays for anti-rejection, anti-clotting and other medication, or for co-pays for other medically needed procedures related to his liver disease and other disorders. We pay all of those directly to the provider and he doesn't even get a check (he took the checks and "cut and pasted" them to make new ones, which he then used with a bank phone app).
But the bottom line is, other than for the straight-up medical stuff, no money.
His lease on his sub-let expired two days ago and we haven't heard from him, which means (I hope) that he has, in fact, found another place to live. He told our daughter he'd had some job interviews, which is better than he did for the 14 months he lived with us.
I really do think that people act differently when their back is against the wall and they believe it.
Jane