I have no idea what they do on the AF side of the house regarding whether or not they'll let you live off base. I'd talk to someone in your chain of command down here before you make any big decisions (though the answer you get now may change by November).
That said, the market for houses right now is very inflated, from what I understand. Because of that, it can be difficult to get a reasonable mortgage that you can cover with rent from tenants. However, with you being a WSO that's going to be sticking around for awhile, it could make sense to buy a place. What I'd do is come down here and look around. Talk to a bunch of realtors, get on the Pensacola News Journal website and look at the classifieds, and see if there's anything you like.
I'd be leery of buying anything on the beach, personally. They are still cleaning up from Ivan and Dennis, and if even a tropical storm rolls through here, it'll be the same story again. My rec would be to get something in East Hill, if you do decide to buy something. Supposedly the city is putting together a beautification project for this area (don't know when) that will make it look a lot nicer. The community is fairly close-knit, there are a mix of low middle-class to high upper-middle class (probably just made a class up there) houses, depending on where you look and how close you are to the water, and you're kind of equidistant to downtown, shopping up at the mall area (south of the airport on Brent), and base that it isn't too bad a trek to get anywhere. A lot of guys live out by the back gate, but the only thing out there besides the back gate is Walmart, and to get anywhere other than that is at least a 20-30 minute drive or longer.
Oh, one thing I'd definitely do before I show up is request a packet of new resident info from the visitor center or some related agency so you can get a street map. I didn't do that when I showed up here and had no idea where the heck anything was for a while. That packet might also have some info on the real estate market.
Okay, this is way too long. PM me if you've got any more questions.
