What you need to do is stay in the flying arena and not in the office (group and wing exec type jobs, not because they are bad, in fact these jobs will help you go far, but they will limit your flying soomewhat). Become an instructor and an examiner and log something preferably over 3000 mil hours to be competitive. Have a minimal amount of checkride busts, preferably none, but one is probably not going to kill you, and of course previous DV airlift in a C-21 or C-9 would help. The 89th will not take you if you are fighter or bomber guy according to their requisites. They are basically looking for the best pilots, in a mature age range as you will be carrying some of the most powerful people in the world around. Just because you meet the mins, you might be too young in their minds. Oh, and this goes without saying, you need to qualify for a higher security clearance as well. This info is for the jobs like at the 89th AW and some of the PACAF and other HQ jobs. C-21s and C-9 positions are out there for guys right out of pilot training. But to get to the Gulfstreams, BBJs, and the 757, its a bit different.
Regards,