At first, he tried getting into manufacturing weapons, didn't seem to get a lot of enjoyment out of it. Then he moved on to working as an herbalist/poison expert. Upon finding out that poisons don't deal a lot of straight-out damage, he's started making inquiries about "buying and selling illicit goods". (He's good-aligned.) He has plans he's hoping to further, but doesn't want to tell me, so I can't really advocate him. I keep trying to ask him what he's looking to get out of the campaign, and he constantly replies "a good story", but then gets REALLY easily frustrated in the roleplaying aspect. At one session he'll tell me he's a hobbit, then this week he said, in all seriousness, "You see...I'm Batman."
My main concern is that he just doesn't seem to be getting what he's looking for out of the campaign, and it's really stressing him out. In the meantime, my attempts to deal with all of his problems is taking a TON of time and will soon start detracting from my ability to provide a good experience for the other characters. I'd really like to include this guy in our sessions, as he's a good friend and it's hard to find roleplayers in our social circles, but this is just driving me nuts.
Any suggestions? I'd be glad to fill in information where needed.