Crew get assigned as pilots, though you can choose which one is piloting. Pilots have a chance to gain experience when they are dogfighting. It does not matter who is piloting the craft except in dogfights. Helicopters cannot have weapons so they are not very useful in this respect (though I suppose they could dodge enemy fire, not sure if that gives experience). Another helicopter vehicle, A LITTLE BIRD, on the other hand is handy for training. Go within the radar range of a cult manor and periodically kill all the spawning hunter-killers.