I'd recommend you store or sell the old car (unless it's a sentimental thing). Have him do something smart like buy a new KIA, Hyundai, or Mitsubishi for $15K or less, with their 10 year, 100,000 mile warranty. I've made 700 mile trips in the Mirage G4 I bought my daughter - wasn't comfortable, but loved 40 MPG.
Yes, he wants to join Navy Federal Credit Union (lowest car and mortgage loan rates he'll find), and USAA (lowest and best car insurance he'll find). Don't use their car buying service, as the dealers who contact him won't budge on price, and yes, you can beat their prices by shopping around.
Dunno if it applies to JOs in their first school, but enlisteds in technical school (in a pipeline, or non-prior service) status aren't allowed off-base during something crazy like the first two or three months. Plenty to do on Pensacola NAS - you can rent boats and fish Big Lagoon, swim in Pensacola Bay, rent sailboats and cruise Bayou Grande. You can spend a whole weekend in the Naval Aviation Museum, and another 3 or 4 weekends wandering the old forts on PNAS. If you ship his jalopy anyway, there's an auto hobby shop on base where he can tinker in his precious little spare time.
There used to be bus service on base that would get a person from the main gate to downtown. Plenty to see in down town. If he gets out to P'cola beach, and he's Catholic, he might be interested to see The Cross in the Sand (and continue on to Fort Pickens). Pensacola was the first Spanish settlement in North America, and the first mass ever was said in the new world was on Pensacola beach.
Oh, and most importantly. HE HAS A GIRLFRIEND! HE HAS KNOWN HER HIS WHOLE LIFE, AND THEY ARE ENGAGED AND HAVE A WEDDING DATE ALREADY PICKED OUT. INVITATIONS ARE PRINTED AND BRIDESMAID DRESSES HAVE BEEN BOUGHT. He needs to name her, and decide on her bio. Back in my high school days, nearly half the senior females would get jobs on PNAS Mainside, or volunteer there (or get fake IDs and sneak into the O-Club), in hopes of bagging themselves a pilot. One skipped graduation so she could marry her pilot, who was shipping the next day. Watch An Officer and A Gentlemen, as well as Surviving the Game with him - he'll feel a little like both Richard Gere and Ice-T at times.
Good luck!