I was always wondering how hard it'd be to get into the (military) school of my choice...
I don't know. I've known several men my age and up who went to the Naval Academy ... their key advantages were connections or sports. This is not to say that they didn't turn out to be decent officers.
And I have friends whose son is at the Air Force Academy; he was recruited for swimming.
Working on your Congressman's political campaign might help you get his attention :-).