It sounds like you are on the right track in terms of prep. I jumped ship at the 12 year point, and had always planned to do so. It was without a doubt, the most stressful time of my life. I put in for seperation with no job at all. Fortunately, I was picked up by my reserve unit 6 weeks later, and picked up by my Last choice major (US Airways/AA) a month before terminal leave.

Prepare your family for a rough year, talk with your wife about this and make sure she is on board. I'm just now recovering (on third year pay) from my first year pay cut ($40/ hour at the time). We cut the budget to the bone, no cable, no Starbucks, etc.

Second, if you do put in your papers, you need a JOB, so don't be picky. Don't be scared of a commute. Military guys seem to be the most vehemently anti commuter that I've met. So take their advice through a filter. I've been double commuting for over two years, but I'm very grateful to have both of these jobs. I am trying to find a local USAFR job, as that is by far the worst of the two for commuting. Unfortunately, it's been a tough nut to crack where I live (and I don't care if I fly a desk). You'll need to take the first airline offer, and then upgrade to a higher choice, if it makes sense later. As time goes by it might not make sense (I've decided to stick it out with AA). You have to take the long view...