Personal Observations; Lessons Learned
In my military community (F-4G), there were two big waves of guys who got out.
The first group was in the 1992-1994 timeframe. I wasn't financially or personally ready to make the jump at that time
Of my associates who bailed, two were hired in fairly short order, one after a year wait, and one didn't get hired....and he was by far the the guy with the best qualifications. He did a non-flying gig in the Guard, and later, picked up a mil-flying gig, which eventually led to an airline gig.
The second wave was in the late 90s. I was a 1998 bailout, although in the Reserves the next day.
At a squadron reunion in 2010, it was surprising how similar everyone's experiences were. The early guys had economic hardships early on (and at the time, some of the early guys were still facing some). Those of us in the second wave had the hardships later.
None of us had seen smooth skies for the entire journey. The guys with the happiest histories had all been in the Guard or Reserves during our airline tenures.
While timing is 99.99% of everything, no one knows what the future holds. Having something to fall back on---mil retirement pay, a Guard or Reserve job, or your own business--is often the only way one can justify taking the risk.