Your son has the persistence for a service academy! Tell him that he can e-mail me if he has any questions.
Better yet, he should talk to a retired Marine O-5 (USNA '90) who's just a few miles away from him in Norfolk: Rob Aeschbach at
Norfolk Financial Advisor – Fee-Only Financial Planning For Military Families
I mean this seriously; Rob just started his CFP business and has been helping servicemembers with their finances for years as a volunteer at the Navy-Marine Corps Relief Society. He gives away a great NMCRS military-friendly budgeting spreadsheet. Our families hang out together at FinCons, and Rob was a big help when my daughter was squaring her own finances away in Norfolk during her training. He'll help your son with any questions about either finances or USNA.
RobAeschbach@Gmail.com.
Nico's or Uncle's Fish Market. But you can get good fish at any of about 250 places on Oahu...