Not having manned aircraft flight time in the past ten years is probably going to be a hinderance for you. You’ll need 25-50hrs in the last 12 months to peak a regionals interest. Cessna/Piper time is okay for that though. The AA Wholly owned regionals (Envoy, Piedmont, PSA) are supposed to pickup on FO hiring after Jan. I’d build some flight time doing a instrument work and apply to them, Endeavor, Breeze, Frontier and Spirit etc. basically anyone who competes with United for business, then go over from there.

Only one regional out five cared that i had ZERO time in last 5 years when i applied. Within one hour of submitting my apps (was waiting to upload my medical) i had a call. Within 24 hours 3 interviews scheduled. I no kidding have a friend who last month had a CJO from envoy within one day of submitting without an interview or talking to anyone.

Ok, I’m going to try Charter first, then the regionals. I do have 25 + recent hours in 172/182s. Looking at Global X, Flex Jet.

If you mean “my first preference is charter, second choice the regionals” yes
If you mean fly charter then fly regional then fly major, no. Any fresh turbine time should get interest from the majors. Make sure you don’t get anything with onerous training contracts

Quick question, what’s with the hesitation about going to get current at a regional?

IMO A great call. I'd much rather be at a place like flex jet or net jets when the music stops vs at a regional. Plus at least flex Jet's organic or confirmed ticket commuting could prevent another move to a hub.

But this was in 2018 when you applied to the regionals?

was going to suggest same thing, spirit or frontier also might take you

The main reason I don’t want to go to a regional, and prefer fractional or 135, is because I’m not within commuting distance and the reserve time would suck. Plus I’m close to a city that is a domicile for both Flex Jet and Net Jet. So that schedule works way better for me.
I did apply with Frontier but they said to get my ATP and then they’ll take another look.

Airline Interviewer: “Show us how you’ve been willing to invest in your transition from the military to a lucrative airline career.”

You: “I’m not.”

Airline Interviewer: “mmmmkayyyyy”