Military aviation is out, he's way past the age cutoff + waivers (not many waivers these days anyhow).

For the OP, yes it's entirely feasible, age is not an issue especially given the clear demand for pilots due to retirements over the next 10-15 years. Where age can be an issue is older folks tend to be less flexible as far as moving and lifestyle (family, financial obligations) so they tend to not be as aggressive at making the career moves needed to progress (or jumping through major airline application hoops).

1. No family makes it easier. Ideally you wouldn't have any obligations like real estate which would keep you tied down somewhere.

2. It's good that you already fly. Anytime someone talks about blowing a bunch of money on career training, I tell them to go get a PPL first and if they enjoy it then come talk to me. If you don't have one, I would get an IR on your own before you commit to a career. If you struggle with that, 121 aviation might not be a good fit for you.

3. Given the rapid pace of hiring and career progression, at your age I would probably do an accelerated program (pay out of pocket if at all possible). Get your seniority asap. When I was in your almost exact shoes years ago I took a more measured approach, and that paid off when everything came to a screeching halt for about ten years and I had to stretch the finances for longer than planned. But in your case, that situation is very unlikely. The retirement numbers do not and cannot lie...unless the US airline industry shrinks by about 70% hiring must occur. They might dull the edge just a tiny bit by extending retirement age to 67 but that's about as far as it will go IMO. Even if they extended it to say 70 there would be few pilots who desire to work that long, and even fewer who could pass a medical.

Easy to get CFI jobs. Very easy. Just don't sign any sort of training contract unless...

1) You're CERTAIN it's a good place to work AND
2) The contract will expire before you reach airline hiring mins.

Answers in red.

Do it
 

Similar situation as you, however I am 43 and doing this... Follow your dreams and dont have any regrets. If you truly love flying you will find a way to adjust to the lifestyle, money scale, and what it takes to get all of this done.
I started flying when i was 19 and quickly ran out of money and the job market back then was really bad. Hence the dream faded and i found myself in technology. Had a very successful career for the last 18 years but the dream was always nagging at me. I worked very hard to get debt free some years back and have been piling up cash since then. I also have a wife that is very successful in her career so that is a huge help, however i can tell you that i would have done it even if she wasnt here.

I initially considered a school like ATP, but after really sitting down and crunching the numbers, I decided against it. I decided to buy my own plane ( a 1966 182J ) so i could crank out some hours and fly all i want when i want. I quit my job about a month ago and have been decompressing and digesting that crazy decision during the last few weeks.. while flying on average 15 - 20 hours a week. I have a handful of instructors here that will push me through all my ratings and I will be done within about 4 months from where I am now.. perhaps sooner if i hunker down and schedules allow.

I got the 182 only because i wanted to be able to really cover some distance with my wife and 2 boys and still have full fuel :-), but obviously there are much more affordable operating cost airplanes. I also have a handful of other pilots that are trying to build time that i do the cost sharing safety pilot with. That brings my direct costs to about $25/hour. Covered T hangar ( open on two sides but out of the sun and rain) is $130/month and my insurance is about $800/year. We will see about that annual coming up in 6 months :-)

Dont have any regrets. I have spoken with a lot of folks who have done the same thing and the overwhelming response is they are happy they did. A bad day flying is still better than a good day in the corporate rat race driving a desk and a laptop in my opinion. You will get a lot of opinions here.. from the horribly jaded to the uber happy.. just keep in mind they havent lived your life and dont have your experiences.
Manage your risk, money, and direction and you will be fine. Do the countless hours hours of research on where you want to be and the path that will get you to your goals the quickest. i am not totally decided on the final path ( airline, 135, fractional, etc).. i think conditions, market, economy changes could definitely shape that over the next year or two.. we shall see but i do know i will just keep my head down and push forward.

oh.. regarding parairie air service.. i talked to him the other day and the recent 2014 changes in ATP and a lot of folks 2 year window expiring here in August. he is booked solid for the next 8 months.. wow.. was going to head over there for some multi time building.. but that is off the table now. Not sure how that affects the regular students as opposed to the multi time building though..

Have fun and go for it.. let me know if you are in the Kansas City area.. we shall go burn some fuel....

kcartwright27-
Hey just curious where you are at in your flying career? Did you make to the Regionals or are you instructing? It has been over two years...