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.