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I've got a similar friend who just can't seem to get it together. I helped him buy a place about 5 years ago but it was only about 5 grand to "help out" and I had the extra so I didn't hurt myself to do it. It made a big difference for him and he got things together a little bit better after that. I would say that if you are that close to this guy buy a car but rent it to him at a low monthly rate that he can afford till he pays it off. If he can't handle that, just take the car back and sell it. That would help him out of his current situation, make you feel like you did something to help, and enable him a little less than just giving him a car.
Make sure you do some kind of loan or rent to own contract if the car is that much of an expense. Just a thought.
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