I understand the wish to get your certs and get the ball rolling by patronizing a zero-to-hero outfit like ATP or Prairie, but for late middleagers going wholehog into flight training is a big gamble and it smacks of midlife-crisis desperation. What if you find flying isn't all you thought it would be? How can you be so sure it is if you only presently have a ppl? It would be tragic for you to your nest egg or most of it just to find that hey, this isn't all that fabulous it's another form of work and not a very lucrative one.

On the other hand, if you took one rating or cert at a time and spread them out savoring each one, you would definitely have an idea where you stood and might even decide to keep your old job and instruct on the side. I savor each rating, signoff, and certificate and chart my next course using the last. Also, what about all those intermediate activities like banner towing, airplane ownership, flying 135, sky jumpers, etc. when will you do those? To me it seems foolish to use the fast track programs to skip ahead if you are over 35. I got bit by the aviation bug at a later age (35) but I am not lured by fast track programs because airline aviation is volatile and relatively low paying. I can see some disappointment in my friends who went for it at a later age- the low salary and hard working conditions are pretty tough.