Isha,
Thank you for a well written and thought out post on a very important subject.
How far did I need to go?
My decision to go was not an impulsive one by any means and was thought out for many months. The catalyst that stated me thinking was the passing of my parents. I felt I was now completely free to decide my own path and let go of the role I had played as their son without their influence, positive or negative.
Another factor was I'm semi-retired so facing employment discrimination would not be a deal breaker. And I spoke to other members of my larger family and they were supportive, as I know this might effect them to some small degree.
But with these issues out of the way I went out and faced my fears with a smile on my face. I have never looked back. I can say it's not for the faint of heart, especially when I don't "pass". I don't look like a man and I don't look like a woman. But a happy smile and a good attitude will go a long way toward acceptance.
I would not wish this life on anyone because it's not easy to be different and go against the stereo types of gender presentation. There might be unknown consequences that if I knew them might put me back in the closet and give me nightmares. But I also did not want to go to my grave having regrets. I want to live my life to the fullest.
So... for me... this is how far I needed to go... in my journey to be my true-self.