[scottmandue]

Buying a guitar is like buying a Porsche, if you don't take someone who knows what to look for you may end up with a piece of junk (no matter how much you spend or what make you pick) Some Fenders are made in Korea and are.. um... less than ideal.
Find someone who knows guitars and have them help you pick one out.
And yeah nothing will turn a person off to the guitar faster that trying to learn on a piece of crap.
I have played for fun for over ten year and never made a buck or got laid because of it although it CAN be a positive experience, If he gets into it he can learn:
Time management (planing rehearshal, gigs, parties),
Practiceing skills ( the music doesn't just fall out of the sky!), Interperonal skills (learning to get along with other band members who you need to make music but you may not like very much)
Money management (If you make any, dividing it amongst the band, subtracting expenses, etc.)