The soonest I see you getting an AFRC UPT package in, picked up, get dates, go to OTS, go to UPT, go to the C5 course, and return to your unit is 2.5-3 years. Then you’re looking at at least 3-5 more years having to fly a ton at the unit getting enough hours there to be competitive for a major...I’d guess getting enough time in 3 years would be pretty tough to manage, so probably closer to 5. Not sure how long it takes people to make AC in the C5 community, but that could/would potentially affect when you were competitive for a major. I’d say the soonest you’d get to a major is 6-9 years from now if you go the military path, and 6 would be pushing it and needing to fly a ton at the unit. If you went to the regionals in a year, I’d think you’d be at a major in 5 years from now with the projected hiring numbers that are out there. Who knows though. Lots of variables, lots of unknowns for each path. But the hiring wave has started. I wouldn’t want to be on the backside of it, where a year or 2 or 3 makes a significant percentage difference for the entirety of your airline career.
You have the mil benefits and the mil network and can get a mil retirement as an enlisted guy. And you’re already a CFI close to being at a regional. Is it worth starting over at this point and signing on to big blue for another 12-13 years from now? If flying military jets is a dream you want to see through and your family is good with it, then go for it. But in my opinion you’d probably be at a major sooner going the civ route, with better long term pay/QOL. Tough call that only you can make.