Does he really love airplanes and flying, or does he just want the uniform? Or the glamour? (Gee, I'm still looking for that)
Its a simple fact that to be a pilot is much like being in the entertainment industry. You have to want it awfully bad, keep your nose clean, and, yes, actually have some talent. The personal price is quite high. There are few really great gigs.
I like my job and can't really see doing anything else. But that's my deal.
Good luck (and stay out of debt)