IMHO, going military is the best way to go. He will have the best training, and get far better "real world" experience. He must be in perfect health including 20-20 vision, so a thorough physical including an EEG and EKG wouldn't be a bad idea. Even if he goes that route, highly recommend he gets his private pilot's license before joining. What that will give him is more confidence in the air from the start. If he has a preference for a service, try to find an ex-Navy/USMC (or Air Force) pilot as his instructor. Doing a little instrument training would be a step better to give him an idea of what's going on during instrument flight. Definitely do the ground school classes! I didn't include the Coast Guard since their pilots normally do a "sea tour" before going to flight school. If he goes that route, suggest he apply to all of the services. Navy, Air Force, USMC and Army, and not lock onto just one service. As an example, a cousin and I both graduated from VT at the same time. I went Navy and he signed up for an Air Force slot. I went into AOCS and straight to flight school. He eventually "aged out" (i.e. turned 29 years old) waiting for an Air Force slot, and never got one. Good luck!