gtnbzy-
I am 39 and can relate to your situation because I too saw aviation as a ray of hope for a somewhat troubled middle age, and wanted to act on it and maybe even fly professionally. I am an educated, emotionally stable, thoughtful person who studies things very carefully before acting. Having studied the life of an airline pilot for a number of years with a view toward doing it myself I have come to the conclusion it's a rather hard life at the lower levels. I am quick to qualify my statement, the needs of the individual may make it an appealing a career choice given the right combination of needs. I have a dear friend who was a successful engineer who at 35 said to heck with this white-collar sweatshop job (his words), I want to do something fun for a living even if it doesn't pay very well. He is currently a new captain at Expressjet, having started from a student pilot around 1999. He likes his job.
In my case, I have student loans to pay and making one third of what I can make performing engineering makes this an easy decision in favor of the latter. In other posts you said you have a fairly high income, so for you income is not as large a factor in the decision than self fulfillment, and this will play a larger role for you than it does for me. For me, just knowing that I could be an airline pilot if I wanted to is enough and I do not feel a need to prove it or actually go out and do it. I am reassured about this state of affairs. The panache, challenge, and thrill of being a professional pilot appeals but is not worth the financial loss or the throwing of my life into a tizzy to obtain, and regional airline flying will most certainly do this for several years at the very least. Airline flying is a devoted, challenging, demanding job and if you are not determined it's for you then you will drop out of it after a very short while. It happens all the time. If I were you I would keep working at what you do now, take a ton of flying lessons, and learn more about aviation. You will have many good years ahead of you when you get to the point of applying to the airlines, even if you go the slower route of taking lessons with an FBO or a flying club, and you will not run the risk of screwing the whole thing up out of rushing into it. If you think airline flying is a cure all for middle age depression, I am here to claim that it is not.
On the other hand I love all things aviation. I currently design the innards of the airplanes every person in the world will eventually ride on, and I drop people out of an airplane on weekends for fun at a skydiving firm. I plan to get on with a decent regional airline in due course of time and fulfill my silly dream. I have no doubt that I will love it even if I make only $16,000. Perhaps I will see you there

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-Cub