I don't think it has to be that hard...I bought a small plane from a Navy pilot (an instructor for F-18s at the time). I asked him how he got the job, and he said he joined on a whim, after being recruited at the mall. The deal he got when he signed up was he'd get to be a pilot as long as he didn't wash out of the program.

(I also spent an evening at the bar w/ a class of his students. I was expecting super gung-ho jock types, but they were actually very laid back and a little bit dorky. Interesting experience for a boy raised by hippies in the Oregon woods.)