I'd say the hardest part for me has been "getting over it". I had lived full time for a period years in the past and had in the 90's returned to some crossdressing and dual living, so I thought I understood the RLT environment and should have little problem with it. How Little I actually understood or knew.
At first I was still some years away from beginning Hormones and other problems had to be addressed before this step could be made, but I made public the identification and began living my new life anyway as I felt I had no other choice. There were the fights and misunderstandings with my wife of course, but that was simply a bumpy road, then my job went down the tube and a lot of influentual contacts along with it, but I used other skills developed in younger days and managed a living.
Using some of my last existing true friendships, I located a new job in a new location and went through the process of therapy and hormone acceptance and began life again from almost total scratch in an area I had never before spent time in or was known to anyone in regards to my past history and forged ahead.
It was during this time that I began to truely learn about the social aspect. Before, there was the intolerance of course, but it was always somewhat "toned down" in my case as most people were well aware of how I could and could not be treated in a safe manner and made a lot of allowances for me they would not likely have made for others. In my new location it was different as I was nothing to them other then another Queer, but at the same time, there was more acceptance of diversity and the environment should have been ideal for me, and has in fact become so, but I had brought with me a highly aggressive defensive posture and attitude that detracted from my personal goal of total integration.
I was my own worst enemy in this goal, as just as I would seem to have achieved it, something would occur which would bring out conditioned responses and actions which were not forseeable in my common everyday presentation, thus accenting my differences from naturally born and raised women, and making what I truely was all that more apparent. Even among those who accepted me as female, there was doubt I could ever be a socially acceptable woman, as I could not seem to grasp the concept of dealing with adversity on levels other then I had learned by prior experience. I all to often acted in a very male like manner when things didn't go my way and it had it's effect on many of my relationships.
In my case, I don't believe True Transition began until I began to understand and address these issues and my reluctance to give up male dominance and power dynamics and accept that I would have to learn to adjust to the second class relationship I now had in mainstream society. An attitude adjustment was needed and so I began work on that both in private and in therapy.
Since I have begun by degrees to rid myself of unbecomming behavior, I have noticed a positive influence on most of my relations and my own comfort in myself. Even relationships which have always been good have taken on new demensions of inclusion which only make me more determined to close the lid on the box holding my past and it's influence on me.
So yes, I would have to say that the hardest part of RLT has always been, simply accepting myself rather then my conditioning.
Terri