When I chose, I just did the math.
When deciding, I figured I'd do 4-5 weeks of IFS at Eglin AFB, 6 weeks in API in Pensacola, almost 6 months of Primary/Intermediate (combined now I guess) at Whiting and possibly another 6/7 months at Whiting if I go helos.
Needless to say, I chose Milton area. I live in Avalon Estates which is just off of Avalon BLVD, about halfway between I-10 and the City of Milton.
It takes me about 1 hour to get to Eglin AFB (which sucks). About 40 mins to get to NAS Pensacola (which sucks). About 15-10 mins to get to Whiting Field.
I'm in the Coast Guard and married with 2 kids.
Fortunately, Whiting Pines (Navy housing in Milton) had no availability for 3 bedroom house. Don't get me wrong, they're nice, there's a mini mart, pool, kid's splash pool, etc, but, eh, half the units still haven't been remodeled.
If you're in the Navy and married, pretty sure you have to check with Housing before obtaining civilian residence.
If you're single, no clue. But as someone mentioned, the rumors are the BOQ is way low on occupancy. If that's the case, odds are that any single incomming personnel will have to live in the BOQ until occupancy is reached.
A good place to look for available houses for rent is http://www.pensacolamls.com/ - just click on PROPERTY -> click the area(s) your interested and hit GO -> click RENTALS -> and select your criteria. Pretty sure there are no apartment listings on there.
I was happy with what we got. The house we're renting had pictures of outside and inside the house. We have about 1600 sq ft, 3 bedrooms, dining room, living room, kitchen, breakfast area, about 1 acre, quite 'hood for $875. Electrcity is about $140 a month (our AC is on quite a bit) and water is like $25. I'm an O-3E so it ain't too bad.
Anyway, good luck.