I can't speak for Guard and Reserve life, where I assume units tend to be more close-knit and family like, but in the active duty world it seems like the worst things someone can do who CAN potentially be competitive for a UPT slot is enlist. Like it or not, there was, is and always will be two different worlds for officers and enlisted. I've known people who've gone every route to go in military aviation. Once you're active duty enlisted, they are not likely to ever let you become a pilot. You can become a maintenance or logistics officer or something else quite easily, but you're just not the same as someone on the outside looking in.
One is a civilian pilot applicant, the other is an enlisted dude who wishes he could be a pilot. The latter sums up a substantial portion of the United States Air Force.
Again, I don't know the guard world. I'm just offering a differential opinion as I've seen it go down.