I'm an Army Warrant with both a Bachelor and Master degrees. I had 2 type ratings (both jet) along with a regional and corporate background when I tried to transfer from the Army Guard to the Air Guard at my same base. I was preparing for my board when I got hit in the face with a memo.
The big change was back in 2011 when the National Guard Bureau (NGB) sent down a memo changing how inter service transfers were being handled. Basically, it changed the game requiring all transfers to meet the same age requirements as a new UPT applicant. Previously, if you were a rated military aviator, age wasn't a factor. Additionally, they were eliminating the fixed wing qualification course for transfers. The Air Guard recruiter called the COL who wrote the memo and had him on speaker phone. He was, to put it nicely, a "jerk" over the phone. It was obvious that he was NOT a fan of the Army.
So, that was that for me. I eventually transferred to the Reserves to fly C-12s. Certainly not KC-135s, but definitely a better quality of life if ya gotta stay flying in the Army.