You may surprise yourself. Do you have the degree and is your medical a solid one? Mind you, a civilian first class won't get you a loadmaster medical on active duty, but if a guard or reserve unit likes you and wants you, they may be able to get you pushed through.

As JohnnyG said that's the key, getting to know some people on the inside...if you want to pursue this route. Networking will be of critical importance if you want to have an enlisted aircrew job with the ANG or USAFR. Few units are willing to hire people "off the street", personally I think this is a bad thing but it's how it is. If you know some guys that are ANG/USAFR aircrew or Pilots/Navigators talk with them to try to get your foot in the door. Don't expect to be immediately embraced, but if you meet some people in the unit you want to work in and they think you may be a fit, doors will open...it just takes time.

This has been an interesting read and you have an interesting decision to make. For what it's worth, I believe that reenlisting in an ANG or Reserve unit would make the most sense. As well, as others have said, you may enjoy deploying to a combat zone, but that feeling will quickly go by the wayside, especially if you are somehow wounded or worse. That said, one cannot overemphasise the benefit of a military retirement, along with the feeling of belonging to something larger than just yourself, and the life-long relationships that come out of military service. As well, you might transition over to the dark (officer) side, which would also help you throughout your work-a-day life.

I mention all of the above, because I was in exactly the same situation as you are, although many years ago. I returned from Viet Nam as a AF E-5 (SSGT) and separated, a year later I joined the Guard, and retired some 30 years later as an O-6. A great ride. Again, I cannot tell you how fortunate I feel to have both a military retirement as well as military health care through the TriCare system. Both worth their weight in gold.

Good luck with your decision.