I jumped at 14 years. The math wasn't relevant to me, the lifestyle was. I enjoyed it so much I stayed part time when some AGR spots were dangled a couple years after I got out.
I am not the sharpest tool in the shed, and I took some risks. However, I had a working wife, a modest house, and a solid ANG gig lined up. I knew there was downside risk but I thought I was prepared. It worked for me.
The guys I know that were at Delta, UAL, and American that got furloughed during that time all ended up okay, but I'm sure it was stressful. I know 4 who made O-6 and secured a full time retirement at that rank. At the same time, I would not have wanted to do the jobs many of them did if I had another option--they worked their asses off and earned every cent they got paid. So--4 quitters I know are all Colonels, and the irony is most did better than the guys who were there contemporaries that stayed in. Then again, we had a superior ANG unit that insisted your crap better be together if you joined them, and everyone worked pretty hard. It was not a weekend flying club nor a place to just cruise a few years.
Like Hacker, I loved flying fighters. I also love flying airlines. I also love flying GA. I think your attitude is about 99% of your happiness. What I will say is doing the part time stuff allows a more gentle mental transition than being "Lt Col Badass" one day and "Mr Jones" in the commissary the following Tuesday. While every guy I know has made that transition just fine, I did appreciate the fact that I got to sort of ease out of the F-15 business on my terms and not just have to STOP abruptly one day and start a new life. It was nice to still be pretty good at something (teaching F-15 stuff) while I was a complete rookie at another (becoming an 727 FE). The social network and friendships were also appreciated. One thing overlooked it often when a guy retires everything changes overnight--work, friends, and often where you live. Flying at your local base keeps a little stability as your world is changing around you. Its busy doing 2 jobs--but I found when I was working by my choice it was simply a lot more enjoyable.
Your million dollar questions should be:
1. Can I survive if the airline industry blows up for 2-3 years? While 9/11 was really just part of the reason things went down so fast in 2001-03, the terror threat to your livelihood cannot be ignored. Do you have a backup?
2. What if nothing happens? Can I stomach going to work for 5 or 6 more years doing the same thing over and over, or will I be completely miserable? One good assignment or something you always wanted to do (command? exchange tour? etc) might make it worth gutting out. Conversely, if you find yourself working in an AOC overseas remote for a year while your old squadron mates pop in and out on an AEF or channel mission telling you about their great new airline gig, you are going to be pretty depressed that night at the DFAC.
For me--it was a bus ride. In 1997 I rode a cattle car from Germany to ATL for a WSEP deployment at Tyndall. The deployment commander was a mx major (I was a capt/flt CC) and had our squadron spread across 4 busses going from ETAD (Spang) to Frankfurt. He had assigned seating. He separated the pilots into 4 groups and spread us across the buses. I rolled with it...
When we landed in ATL on a Friday night, something happened that prevented us from flying on to Tyndall, so buses were chartered for the 6 hour ride on to Tyndall. At this point--quite tired of all the adventure and being treated like a third grader when I was an early 30's F-15 IP, I asked if I could peel off, grab a rental car with several of my fellow pilots, and go catch an AU football game the next day. We would be down at Tyndall by Sunday morning and would be there for all mandatory indoc stuff that evening. Our DO--who at the time was a 2 ship flight lead and not an IP, pointed out I it would be disrespectful to the Mx Major and we needed to be team players and ride along on the bus. He didn't want to rock the boat and explained we were being selfish and not team players. The fact we were on the road 120+ days a year, rolled through an ORI recently, etc etc really didn't matter. What mattered was we all needed to be treated the same, and we need to make sure we didn't hurt any non-pilot feelings.
As I rode down the Georgia highways that night, dog-ass tired and disgusted with being treated like a child, I had a "Scarlet O'Hara" type moment where I said that "As God is my witness, the first time I can get out I will never let anyone make me do this bull**** again...." It wasn't flying combat away from family, or long nights in the vault, or the wear and tear on my back that drove me out. It was being forced to sit on a bus...in assigned seats...because someone up the chain didn't have the balls to make a decision and let us simply manage ourselves during a routine peacetime deployment. I knew I always wanted to be an airline guy anyway, but that night/early morning was when I simply knew it was over. It was four years later before I could see daylight, but I never wavered a moment after that trip.
Sometimes when I fly into Singapore or Seoul now as a 767 captain, and the limo picks us up, I still think about that time. And I smile. I don't get to shoot aim-7s anymore, but I also have tremendously less bull**** in my life. And I have a lot more money. I can live with the tradeoff...