[skydog]

There are always going to be "what ifs" in life, not matter what decision you make. "What if" you make the change to aviation and then lose your medical in 5 years? Will you spend the rest of your career wondering "what" your life would be like "if" you had chosen to pursue something other than aviation?

That said, if I were you I would stay away from aviation, and here's why: You don't sound as though you are fully committed to it. Aviation is a pursuit that is not for the faint of heart. If you are not prepared to give it 100% and persevere regardless of the obstacles, then you ought to consider another line of work. Consider that you even if you give it everything you have, you could still wind up spending your career job hopping at third-rate operators. I've known plenty of well-qualified pilots who spent their entire careers doing that because they were never in the right place at the right time.

Now consider your age. I'm guessing you are 40+. Figure two years until you are minimally qualified to instruct. Another year or two before you are qualified to fly for a commuter. 5 years there and then on the majors (assuming any are left). Now you're in the right seat with 10 year + upgrade. You might make Captain by the time you are 60, you might not. That's assuming you don't medically dequal before that (I've read that less than half of pilots made it the old mandatory retirement age of 60).

Now consider your family. For the past two decades they have lived with all that goes with a military life, and have probably done so uncomplainingly. Although they may not have said so, I am guessing that they are looking forward to having you home. To retire from the military life and go in the airline life...well you might as well stay for another 10 and get a full retirement.

I don't know what kind of opportunities there are for a retired military intelligence officers, but I imagine that there are some, and they are probably more lucrative than anything airlines or aviation can offer, at least within the time frame you have to work with. If you "just wanna fly" then I reccomend getting your ratings through instructor, and doing that in your free time.

Heck, you could even stay in for another 10, work on your ratings and build some hours along the way, collect that full retirement, and still have another 10+ years to enjoy an airline career. Believe me, 10 years is enough.

To sum it all up: Given where you are in life; family, financially, and career wise, to me the numbers just don't add up to pursuing an aviation career. If your demographics were different I might advise otherwise.

One other thing: So many people show interest in changing careers (to aviation or otherwise) because they are not happy with work. Maybe I am in the minority here, but to me, the purpose of working is so that you are better able to enjoy your time away from work.
If you enjoy what you do, but are never home because of work, then what's the point? That's the reason I left the airlines after 10+ years.

There you have it: my advice. Worth every penny you paid for it.