I don't fit your category as although society has always placed me in the Crossdresser category in my mind it's always been much more.
Would I transition if all the barriers were gone, absolutely yes, but they are not so it's a moot point.

I always desired to be female. Unfortunately, when I was younger the support wasn't there and neither were the finances. Now that I'm much older it's the opposite. The support is everywhere and I have the financial ability to proceed. Life however has dealt a cruel hand in that with age has come medical issues that preclude safe surgical procedures of the extent needed to fulfill my lifelong dream. At this point I've decided to go on as I am and hope that the next life (if there is one) sees me live my dream.