Most of us have been where you are. Obviously, there are no guarantees. You have to decide if the goal is worth some risk and if you can step off the edge.

Recent years and the near future will arguably be the best opportunity to get an airline job over the last 20 years. So, if you're going to roll the dice, this is probably the time to do it.

I think you have two choices:
Stay in, take a reasonably sure thing and postpone your search for a life after until you're in the check of the month club. You give up potential seniority, risk leaving from a desk non-current and entering a stagnant hiring market after the wave. Kids may be approaching college age where thin paychecks may be even less workable than they are now. It's also possible the job market will still be good or you'll have some more flexibility to take a regional job if necessary.

Or - you network like crazy over the next 6 months and get yourself a guard/reserve job. Get yourself that safety net, put your apps out and take the leap. Maybe you're one of those lucky guys that ends up in basic indoc at a major airline while still on terminal leave. If not, you guard bum and do what's necessary in the interim until someone calls you for an interview (and bring your A-game to it - 'cuz it ain't a sure thing).

Either way, I highly recommend doing whatever is necessary to get a military retirement of some flavor. Good luck.

P.S. Maybe things have changed, but I applied for a DOS and heard crickets from the airlines. I got close and pulled my papers putting myself back into the assignment process. It took a few months for that to work through the system and I started hearing from the assignment guys. I re-submitted my papers and established another DOS as far out as they'd let me (short of IPs at the time). I think I got another 9 months which allowed me to line up the guard job and go from there.