1 and 2 are dealbreakers. Just 1 alone raises a giant red flag. I don't think I would have the stomach for that. I did date somebody who was unemployed for two months, and I felt cruel breaking up with him "just because"... But he was too unstable. And also a jerk.
13 is a just a bad idea all around.
14, if I was experiencing it, would be extremely flattering at first. But then after a while it would become extremely tiresome. You cannot be his sole go to human crutch. It's simply not sustainable, and it really isn't fair.
What makes you stay?