First off, I'm sorry to hear this. It must be hard on you.

I was wondering if he is not working due to his bipolar? If he can't financially pay for meds, he might be able get help with Social Security if he is deemed disabled.

I do believe you are enabling him and doing so will not help him get on his own. You said he was on meds, is he in therapy too?

Good luck and keep us posted.