IA, Comm MEL/SEL then CFIs
Hey,
You have a BS and an A&P. All you need is the remaining ratings through CFI. Since you are going to be in the military for the next ten years, I would get to the CFI level and instruct.
Use your VA benefits to get your ratings and for building multi time. The Masters is a waste of VA money unless you have some need for it in the military.
Getting on with a Corporate Department is all about who you know. It would be tougher to get that gig than to go to a Regional Airline.
I don't know what your age will be in ten years but remember you can work in 121 operations now until you are 65.