If I were you, I'd find a good regional with a west coast base (XJET, Eagle, SkyWest and Horizon come to mind) where you could make good money (relatively speaking. You get to the high end of the pay scale at any of those companies and you are making $90,000+ per year) and enjoy a totally decent quality of life. Sounds like you aren't hurting for money so take your 18 days off a month plus vacation time at those regionals and enjoy the travel bennies to travel the world while getting a paycheck from your business and the airline. I just look at it this way:
You're 38. Lets say it takes you a year or 2 to get current and comfortable with your flying (I am assuming you've already got all your ratings and 600-700TT/50ME). Now you're 40 and get on with a regional. You spend 5-10 years at a regional now you're close to 50. That really only gives you 10-15 years at a major. This is how the money breaks down with some rough numbers. Bear in mind that these are conservative numbers, shooting for middle of the road on pay, not taking into account furlough or concessions and about 900 hours/year (75/mo). They also don't take into count down time from training cycles, loss of vacation and sick time when you change companies and the quality of life hits you get when you are a junior FO and a junior CA both at the regional and the major.
Year Position__Earnings
1......Regional FO...21,000
2......Regional FO...36,000
3......Regional FO...39,000
4......Regional CA...61,000
5......Regional CA...64,000
6......Regional CA...66,000
7......Regional CA...68,000
8......Major FO.......32,000
9......Major FO.......56,000
10....Major FO.......66,000
11....Major FO.......72,000
12....Major FO.......77,000
13....Major FO.......79,000
14....Major FO.......80,000
15....Major FO.......82,000
16....Major CA.......130,000
17....Major CA.......133,000
18....Major CA.......136,000
19....Major CA.......139,000
20....Major CA.......141,000
21....Major CA.......143,000
22....Major CA.......144,000
Total Earnings: $1,865,000

For these numbers I assumed you'd look at a "career regional" like Horizon, which is where the numbers come from. Horizon also has one of the best 401K matches and work rules in the business.
Year Position__Earnings
1......Regional FO...26,000
2......Regional FO...36,000
3......Regional FO...38,000
4......Regional FO...40,000
5......Regional FO...42,000
6......Regional FO...44,000
7......Regional CA...70,000
8......Regional CA...73,000
9......Regional CA...76,000
10....Regional CA...86,000
11....Regional CA...88,000
12....Regional CA...91,000
13....Regional CA...94,000
14....Regional CA...96,000
15....Regional CA...99,000
16....Regional CA...103,000
17....Regional CA...105,000
18....Regional CA...109,000
19....Regional CA...110,000
20....Regional CA...111,000
21....Regional CA...112,000
22....Regional CA...113,000
Total Earning: $1,762,000

So when you get down to it, the total earnings are not significantly different but you quality of life won't fluctuate once you get a year or 2 under you in your seat. You'll find when you get to the majors, where movement is much slower than at the regionals, that you may be "junior" for a long time. Whether that means more time on reserve, less desirable trips or lower paying aircraft, it all impacts your quality of life. So if it was me, and I didn't really need the money because of my second income stream, I'd enjoy the lifestyle, get paid to fly airplanes once in a while and enjoy the good life.