I retired from the AF in 2003 after flying the C141, C21 and as an Army Warrant flying helos. Luckily I did the whole 21 years flying and my be all, end all of human existence was an airline job flying the 747.
I had an interview with American the end of Sept 2001 and was supposed to retire Mar 2002. Well 9/11 took care of that plan and I was stop lossed for a year.
Good thing as there were zero flying jobs after 9/11. I retired a March 2003 with about 7000 hrs, tons of international and IP time, but without any prospects. I applied to every carrier known to man, but there just wasn't anything out there.
In the meantime, I taught classes with Embry-Riddle, flew day rate on a Jetstar II (huge POS), Citations, Lears and finally got a gig managing a 2 airplane Part 91 flight dept in Mobile, AL.
2 years after retirement, I found my current gig goofing on Monster.com. Now flying a G550 for a Fortune 100 company and making pretty good coin, tons of time off and great bennies.
I couldn't go to an airline job now under any circumstances, I'm too spoiled flying Part 91.
A flying life after the AF is very doable, even with a break in flying like you have. Get that ATP and put yourself out there. Check every free pilot job site everyday and send out a 1000 resumes. There are many corporate outfits that hire on personality, not type ratings.
If you must fly for the airlines, then it will probably be a regional to start off. I never did like that option.
You are right about one thing, Tricare Prime is the best thing besides the check you can get for your service.
Good luck!