I have about a half hour commute on a normal day too (up the turnpike to Lewiston), and the longest it's ever taken me to get to work is 45 minutes. Driving can be rough when the snow/sleet's still coming down, but like NavAir said, they're great about getting roads cleared quickly.
Almost all of the single guys in 26 live in the Old Port (home to Portland's bars/non-chain restaurants, exactly the opposite of the NAS Jax area). One thing to consider - a lot of the apartments downtown don't have designated parking spots, and during snow storms there are parking bans on the streets. If you're looking for a more traditional apartment building, you might want to look up Back Bay Tower. It has underground parking, and it's in a decent location.
For what it's worth, I don't know anyone who has started their tour in Portland and moved closer to base. Brunswick is quaint and New England-y, but for us it got very small very quickly.