Downtown,
What is your end goal? You will fly your butt off and your schedule will not be your own. I flew for the majors. I made a lot of money my final year and I was flying the 777. I retired (FIREd at 52) I got my life back: holidays, weekends and I could plan more than one month at a time. It was a great job flying sweet aircraft but it comes at a cost. It's all about seniority. It is a good time for the young pups when they reach our age they will probably have a great schedule and pay. I'm not trying to rain on your parade just another perspective.
Very good question and thanks for the wise counsel/reality check, WT. I will work for another 1-2 years in my current industry (enterprise software), but would like the option of flying multiengine equipment part-time afterwards when I'm in semi-retirement (for pay, even if not much). Working weekends sounds ok if I'm semi-retired. Realistically though, I don't think a regional or major airline job is in my future, given all the challenges with being on reserve, commuting to a different domicile/hub, little flexibility with my time, etc. As to a goal, flying 2-3 days per week in a King Air, or similar equipment, based out of San Diego (we're moving there in the coming months) sounds perfect to me! Of course, nirvana can be elusive and I'm okay if I get pulled into other hobbies/interests. I view semi-retirement as a time to explore, reinvent oneself, travel, take control again (it's my life!).
Congrats on your FIRE and successful aviation career!