"Even if it takes longer to get to a Legacy." When you take longer to get to the major you're not delaying your probationary year, which some think is no big deal. Instead you're sacrificing your BEST years(s) at the majors. At your age you'd be approx. a 20% relative seniority n/b CA in DFW at AA. Pulling down $375K plus another $60K in your retirement 401K. What's the extra year at NetJets/FlexJets earn you? Would you pay $200K to take a year longer to get to the majors? That's the trade off. You mentioned that you have 1500+ hrs mostly military twin turbine time. Majors military hiring percentage is down to 25% +/-. The overall standards are getting lower all the time. You might get hired by a major right away OR would probably get higher by a major within your first year at a regional airline. Get 121 on your resume, a decent size jet type rating, and you'll have a better resume than you do today? How much TPIC time to you have? Not SIC flying the a/c - as first pilot/Captain/signed for the jet? IP qual? Airlines consider 500 hrs TPIC 'competitive' and 1000 hrs TPIC 'highly qualified'. Guys are getting hired at majors with 2500 hrs TT who've only been CFI's and then regional FO's. I'd go to a regional and I"d be surprised if you're not hired be a major - immediately or within your first year. IDK what the fractionals require to upgrade but one company I know of required 3,500 (?) TT to upgrade for insurance reasons.

Airline flying is easier. Yes you fly more per duty period. It's more scripted and consistent. Less sit time = more hard flying time per day. More days off. Can use end of month changeover to make 10-20 day mini-vacations. < You'll work hard the rest of the month to make the mini-vacations.