I've been flying for the Navy for 20+ years and know a lot of guys that fly for the airlines.
I don't recommend flying for the military right now. Things are getting pretty bad with continuing resolutions, sequestration preparations, and significant funding cuts for the past 3+ years. Even if the pressure eases right now, it'll take about 4 or 5 years to get past the challenges we are battling.
Most of the guys flying for the airlines consider it just a job: just driving the bus. More days off during the month that a 9-5 but a lot of time away from home during holidays especially for the new guys. Those airline guys that love flying, do it in a Champ, One Design, C-180, etc, or build their own.
Most of the "experts" are saying that there is about to be a massive pilot shortage and employers are going to start hiring and in droves. That remains to be seen, but even to get hired as a commuter co-pilot you will have to have about 500-1000 hours with some multiengine and instrument time to be competitive. Plan on doing a lot of grunt-work flying to build your time while getting paid peanuts. Even the commuters pay peanuts. Check out the pay scales for each airline here:
http://www.airlinepilotcentral.com/airlines.html .
After several years and a few thousand hours you can apply for the airlines and start at the bottom of the food chain making chump change again for a year or two. Then the money starts rolling in...kind of. Another consideration is domicile. If you don't want to live near your airline's domicile, you'll be commuting for every trip. I've got a bud that flies for FedEx (Memphis) but lives in Montana.
To be frank, except for getting shot at and schwacking the bad guys, I am 100 times more satisfied flying my Pacer than flying Uncle Sam's iron.
This isn't all gloom and doom. If you are willing to tighten the belt for a decade and get your chops in the industry, then flying for the airlines is a good job, can be an adventure, and eventually make some good money. I think, however, with your military experience, you can land a good job getting paid a living wage, gain experience, and have a more stable base for your family. You'll still have to make your chops, gain experience and advance yourself.
But that's the perspective of a 43 year old with 25 years of being on the gub'min dole.