One of the hot topics in the PNJ (Pensacola News Journal) is the housing market. There are ALOT of overpriced homes in the area which is why there are 5,000+ homes on the market. It's not all bad news, but go here and then do a search on the website for other topics:
http://www.pensacolanewsjournal.com/apps/pbcs.dll/article?AID=/20060307/NEWS01/603070320/1006
Now for some of your ?s. I close on my home in Miltown on Friday...so I just went through the purchase process. When I was here the first time, I rented.
I'm tired of throwing away $ on rent
If you take the excess of what you pay in rent compared to a morgage, and then INVEST it, than you're not necessarily throwing it away. Although, property, in and of itself, is an investment. Tax breaks are the other major reason people buy. Rent pays for peace-of-mind though too...so take that in account.
for the amount of time I will likely be in Pensacola, is it worth the hassle of buying/selling a home.
You will be here a while if you get jets. You may not be here long if you don't.
What is the market like (how easy will it be to resale)?
5500 homes. Totally a buyer's market. Resale is easy for any price - given that you have 1) all the time/patience in the world and 2) plenty of money to pay for the mortgage of two homes (or rent on one, etc). Most of us don't have this kind of time...the nicer the home, the closer to base, etc...all goes into the rental market...which around here is actually pretty hot (according to my realtor). So, in summary, resale - not hot, renting - hot.
Are there any specific areas to look at/avoid?
Pensacola, Pace, Milton (latter two are less real estate taxes in Santa Rosa, but start getting into a pretty hefty drive from NASP) are good places to look. Certain areas of Pcola are older (i was actually born in one of these places) and the neighborhoods are different than your "american dream" so drive around during the day and then at night to figure out what you think. Santa Rosa High schools are ranked "higher" on the "goodness" scale, but again, consider the drive (35-60 minutes to NASP).
Should I do VA or conventional?
I'm a big fan of conventional if you have money to put down. There are a lot of creative financing options out there. VA/FHA put a lot of restrictions on a home purchase and then eventual leasing if you are interested in renting it out later, but do offer a way to get a "foot in the door" with little to no money down. The big deal with these are the appraisals...which right now, with inflated home prices, you may not be able to get the appraiser (VA/FHA is a bit more stringent) to apprise the home at the asking/buying price...which means that you have to come up with the difference.
I expect to have about $5k available for closing costs etc.
This should be able to get you a decent amount of options. However, remember that just creating the loans and various other charges, about $3k of that will NOT go to the purchase price...so if you can cash out some stock to get more money, I'd say that $8k is a bit more comfy to close with. For my first home, it was a condo in VA beach. I had 80% into a 5-yr ARM, 15% into a home equity and I brought $8.5k to the table at closing for a 143,000 condo.
I hope this helps a bit. PM me for more details, but remember that the BAH the navy gives you is not intended to be able to purchase a home until you are O-4/O-3E. So, if you were to look for BAH to fund a home purchase, I wouldn't expect that to happen until about 4 years from now.
Good luck.
~D