I am NOT an airline pilot, but like yourself considering it as I look to the next chapter. Full disclosure, I tend to be extremely risk averse when it comes to my family's financial security / stability. From that disposition, my cheap advice is finish up with the FAA (which sounds like is at least workable for you, maybe even enjoyable, hopefully with weekends off sometime soon), get back into flying when and where you can (flying clubs, maybe use some vacation time to work on the ATP), and then hit the regionals with your pension secured and money far less of a concern. This job will still be here in some shape and size when you retire from the FAA, or if it's not (because of a black swan event, global recession, retirement age to 72, automated flying, whatever else could rock the boat) then you'll be glad to have missed the tough times. Your family situation obviously plays big in this, and maybe for good will lower your risk aversion to enable a move like this.

I'm not at all knocking the industry or the prospect of what you're considering, but with the time you have banked towards a permanent membership in the check-a-month-for-life club, in a job / career field that's been solid for you, you're in a good place to keep doing as you are and still do the airline thing again in good time.

Just my $0.02.

Good luck, and may you find all due happiness and success with all of it however it goes.