Wow, dancinginthedark you are good. I have heard many of my Marines tell me they didn't know where to find the uniform regulations, but you found them for all the services.
There are two issues, crossdressing, which is actually easier to do, now at leas, and then there's the transitioning which is where the tough battles come in.
In all those regulations, they don't really specify much detal on what type of under garments they have to be. For most it just uses generic terms, like briefs, boxers, crew-neck or v-neck and the colors white, black, brown or neutral. So If one wanted to, they could go to Victoria's Secret, buy some white briefs and a white crew-neck, marked them properly then technically there is nothing that could be done. Now of course they may try and send you to see a psychiatrist at that point. (I can provide some insight on how to safely do that in the Military latter if needed).
Transitioning on the other hand is much more complex, and the hardest thing to overcome, is that "technically" they look at ones body similar to how they look at "government property". An example would be that if I go to the beach and get a sever sunburn, the first time or two, they might might not say anything, but if I constantly am getting severely sunburned at the beach, then they probably will charge me with something as it will likely be taken as willful damage. Transitioning will most likely be taken the same way, in that one is willfully doing something that affects and prevents them from doing their duty for an extended period of time.
So, cross dressing isn't really that difficult, if approached smartly, but unfortunately, the military just hasn't quite warmed up to transitioning yet.