I wouldn't rule out living close to whiting. Theres plenty of REALLY cheap, but nice houses you can rent within 10 minutes from base. Yes, you're 40 minutes from downtown/beaches, but the money you save can easily be spent on taxis. In advanced our standard weekend practice was to drive a car downtown, park it overnight and cab back and then do a downtown brunch car retrieval in the morning. Sounds like a pain in the ass, but it wasn't that bad. Downtown pensacola isn't so great that you're going to be missing out of an awesome lifestyle by not living within 10 minutes. However, if I were to be spending more time than just primary or advanced in that area I would lean towards closer to Pensacola for long term sanity. Milton does get you.