Welcome, Jigsaw. And welcome to the Real World (as we used to say

).
I retired after 24 years in the military. I worked for six years as a contractor to DoD and the USCG. I did not transition until after that.
I was a closeted cross-dresser during much of the time I was associated with the military. The internal pressure to keep that a secret grew and grew and at times was almost intolerable.
I have never dealt with the VA but know that some do. Their experience is generally good, but it depends on the staff at your office. I began counseling with much of it on my spouse's insurance. I began transition at 65 and used Medicare and Tricare For Life to pay for most of my counseling and hormone treatments. I paid for GRS myself. I am now almost a year post-op.
I had no trouble changing my name and then presenting myself as Kate at the base to get my ID card changed. I had no trouble changing my name on the various records. The only problem I had with any of it was changing my gender with DEERS. I think, though, that it was someone at the office that I dealt with who was dragging his feet. It's all straightened out now.
This is a remarkable journey. I wish you luck.
- Kate