How much is too much assistance?

My son has had problems since HS years probably but was finally diagnosed rapid cycling BP at 28 almost 2 years ago. He responds well to medication but can't afford it so I pay for it - no gripe there (when he bothers to get his meds).. The gripe shows up when I look at how much other financial support I wind up giving him just about every month for his routine expenses.
For years, I felt he needed financial help but now am wondering if I am really helping him; in fact, am I being a detriment to him? That is my first question.

Second: I am considering giving him a lump sum of money and telling him to use it as a cushion, or blow it,
whatever, but when it's gone, not to ask for assistance for routine daily expenses any more. I would still pay his meds and Dr bills (which I have to pay directly to pharmacy and Dr offices; I used to give him the money to pay bills but he started spending it and not getting his meds!). So my second question is: Is there any hope of this arrangement working?
I am open to suggestions; I just don't know what to do; I'm not always going to be here for him......

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.

agreed........you're enabling his behavior. a lot of us have bipolar and work. and as Petunia said, there's SSI......

Thank you very much for your input; I truly Do appreciate any thoughts/suggestions.

To answer the questions:
He has seen 3 different therapists basically because I insisted. He goes a while and then quits explaining it is a waste of my money--I wonder if he goes until they are knowledgeable enough to make suggestions (which he finds undesirable?).

Yes, he does work. He is quite intelligent both academically and in good ole common sense and, I think, could be one of the financially successful BPs.
BUT: he wants No responsibility (is that a BP trait sometimes, too?) so he unloads trucks at WalMart, who is not known for paying well. He talks of needing a better paying job a lot, but Never Ever looks for one...?????

Still very open to suggestions from anyone and Very , Very Appreciative of the 'enabling' comments.

I don't think you can suddenly change the "rules" and have that work very well. Why not get together with your son, make up a "budget" with/for him and try that?

One of my stepsons got in trouble, was spending money for school for other things, bouncing checks, owing money all over the place and got pretty messed up (and didn't/doesn't have a mental illness) financially so my husband did a: "give me all your money" and every week or however often his son got paid he'd come over and they'd look at the budget and my husband and he would pay the bills according to what could be afforded/was due. All that was owed was "known" so he had to get bills out from under his car seat, etc. :-) and he learned about priorities. He'd bounced a $10 check to the grocery store but was wanted in three states by state police for speeding tickets! He was worried about the grocery store, LOL.

Think back to how you learned about money and work life? Like me, you probably weren't ever "taught" anything about it? You have to practice with responsibility in order to learn how it works, just like anything else. We teach math and economics in school but not how to budget and pay bills, use credit, etc. It might be embarrassing for your son and you might want to find a successful male he admires to help? But anything you can teach is probably better than just giving ultimatums without any "help?"