I've heard it's possible to get some sort of "hardship" assignment in order to help out a family member- might be worth looking into. It would probably be easier to get to -135s at MacDill than C-37s, just by virtue of the MWS vs OSA assignment.

There are plenty of young, hard chargers from MWS communities who have a hell of a lot more relevant, world-wide experience to bring to the table than a FAIP, no offense. Plus they've been burned out with constant deployments and the overall stupidity that plagues AMC and active duty. Again, no offense, and I'd bet the vast majority of folks down in the C-37 community at MacDill would agree, but your best route would be to go to an MWS, earn some real credibility, work your ass off, become jaded like the rest of us, and then try for a good deal OSA. Like you said though- you won't know if you don't ask!