There are lot of good points from all the wise people who have shared their views & I am probably the least experienced & least qualified to give any advice, but I will share my thoughts...

Imagine this.... a person turns 60 or 65 one day.

Looking back at his career & life in general, says, "I've done great".
I have decent amount of cash, decent chunk in retirement accounts, rental properties, a nice paid off house in upscale suburbs, nice toys & cars including a CIRRUS or SARATOGA, all paid off... Kids done with college, all settled... No debt, very comfortable next 25-30 years.......

He looks back & asks himself "Is there anything that I wanted to achieve but couldn't do so....." He has reached here but in the process ignored his dreams & gut feelings, taken the practical approach with a safe route that is comforatble & secure.

Then remembers, Oh, I always wanted to be an airline Captain, for as long as I can remeber but I kept putting it off for a later better time.....

Now, even if he wants to & can now afford to do so, Still can't do it... Max his money can still buy him, is a self sponsered type rating with a Pay 2 Fly First officer position in some 3rd rated company who participates in such schemes..... Still not bad, he stills gets to fly the airliner as an airline pilot, but it is not quite the same feeling....

Unforunately, all the money can't buy the 4th stripe.... That one has to be earned......