Beyond thinking about upgrades, retirements, or even the pay, think about what it will do to your life. Do you currently live near a hub where you could get based by the regional that's based out of there? Or are you planning on commuting or moving? You'll probably get tired quickly of commuting from the west coast to the east coast for a job that requires you to be there a minimum of 4-5 days a week. What about after your regional time if you get hired at a Legacy and based on the other side of the country?

I also wouldn't plan on a 3 on 4 off schedule. More typical is 4 on 3 off. And it could be worse. Add commuting to that at it means you'll be lucky to have two or so days a week at home.

Living in domicile the schedules can be great. I slept at home nearly every day last year. Used my overnight bag probably for less than 10 nights and I'm not very senior in domicile. Compared to my time in the military, behind a cubicle, or the other management positions I had before flying, this job head is incredibly better.

If you want to fly, do it. If your only reason for change is you think you'll be making $150K in 5 years you'll probably be pretty unhappy. You may never make that kind of money. Not everyone will get to a Legacy.