Propwash72

New poster here, finally getting a plan together to make the jump from a dead-end IT job to full time aviating.

My situation:

43, married, two kids (teen and preteen)

CFI/CFII, 2000TT, almost 100ME, no turbine. ATP ride scheduled for later this month. Been instructing as a side gig for most of the last 15 years and it keeps me somewhat busy.

My ultimate goal is a Part 91 corporate job with one of two Fortune 500 companies here locally. With a family, QOL is a big issue, almost as much as pay. Relocating is not really an option right now, but may be later. I'm not opposed to Part 121, but corporate flying appeals to me more.

Based on what and who I know at these two companies, it's possible for me to get hired directly in, but I fully expect them to tell me to come back when I have some jet time.

Should I just go ahead and go to the regionals first? I'd need to commute, but my area has good frequent service to DFW, ORD, IAH and ATL. What companies should I consider first, based on pay (which is going to suck everywhere, I know), QOL, upgrade, etc. My ultimate goal is Part 91 corporate (or NetJets), but a regional with a good flow agreement to a major would be good too.

Does anyone have any side work/businesses going on to take some of the sting out of that regional pay? If so, what?

I busted my initial CFI and ME rides almost 20 years ago (young, dumb, unfocused, etc). I've had 1700 or so incident-free hours since then. Any concerns here?