I have three letters for you....A N G
You can have your civilian career in IT.
Go to school at an in state school tuition free ( this is a National Guard benefit and not Reserves) while holding on to your GI Bill earned on Active Duty for later endeavors.
Work in a career field as close to the flying operation as you can. E.G. maintenance, load master, flight engineer. It looks like your background would make you an easy transition to either of these career fields.
When your degree is complete, apply for a commission and a pilot slot.
You have about 6 years to make all this happen. You could be established in your IT career, and also be marketable to a regional if not major airline by 33 and be debt free.
Lots of threads on this. Find someone you went to high school with who is on this path. I bet if you look around hard enough, you will know someone doing something similar.
From the school you mentioned in your thread, I'd knock on the door of the C-130 unit in Savannah, and also the Charlotte, NC unit.
Good luck and thanks for your service!!