If you go E-6s though or are Coast Guard, your chances of getting picked up are very slim due to the limited numbers.
Not discounting your point, but a TACAMO guy I went through OCS with got picked up at the end of his second tour as he was PCSing to das boat. Not sure how many times he applied, but for as few guys I know who have done it (if I can even think of any others), I know a TACAMO test pilot.
Yes. My point was that winged options aren't currently being pursued, for whatever reason- presumably due to high cost and long time to develop.
I won't proclaim any expertise in the field anymore, but somehow my memory tells me, when I was in spacecraft design, that the winged options are not very efficacious or safe. The STS (shuttle TRANSPORTATION system) was designed specifically for quick, affordable, and quick-turnaround trips to low-earth orbit. The achievement of those goals is dubious at best, as it wasn't very cost effective and took far longer to turnaround than I believe they were anticipating. Not to mention the program was cut far short of its original planned goals.
Modular rocket designs are far safer, as the manned module at the top has a rocket escape system that can pull it away from the rocket it sits on top of, if a catastrophic failure occurs. It also has a heat shield that is protected on launch, and has far fewer areas for potential material failure (landing gear doors, etc).
So again, my expertise disclaimer aside, there is a reason winged vehicles are not being pursued for the future of manned spaceflight. That being said, there are other designs for quick return or quick orbit shuttles that have been tested (X-37) and may perhaps be used, but not for the longer/farther trips for which we are planning to the moon/mars.