What rank do your calculations assume you will hold at retirement? O-5 is not a guarantee, especially in this fiscal austere uber PC climate. Say the wrong thing or do something perceived as wrong and you could be on the RIF list.
How is your health? What is the family history? Any heart disease or cancer? Are you taking action to prevent those diseases? I think I'd rather be on airline disability, if those unfortunate things occur than to be medically retired from AD and maybe unable to obtain an FAA Class 1.
Getting an airline job under 40 and being in the ANG/AFRC (if your family can handle the lifestyle) before any of the things happen that have a higher likelihood of happening as we age would seem to be the better plan.