Is this the son I met a couple years ago at the TRE Hangover Run?
The other thought, particularly if your son is serious about going to a military academy, is to see about getting that congressional letter of recommendation necessary for the application. IIRC each congressman/senator (and the VP) is only allowed 2. It could be very easy for those to get "used up" if you ask too late in the application season. Though I've also been told that if an applicant is strong enough, they can always find a letter for him.
My eyes are/were bad, as DODMERB reminded me when I was in HS, so flying was never a possibility for me. Best of luck to your son.