1. Guilt of doing this to my wife, but based on how she's accepted other things about me I am hoping for a good outcome.
2. Fear of kids being bullied because of who I am (your daddy is a tr***y!!!)
3. Not growing up in my correct gender, especially with regard to school. This is a big one. I went to boys only schools, but we did have a few girls in 6th form who were there by exception, they were there to do specialized subjects only we offered. I so badly wanted to be one of them, but I also wanted to attend either a co-ed school or one of the girls' schools. I really did not have a choice though. I am pretty smart and the schools that offered the subjects my parents wanted me to do and were close enough to home were boys (and girls) schools. I was actually not only top of my class but top of two primary schools I went to, by far, in fact. So I passed my entrance exam and could have gone to any school that I wanted. My parents chose the school for me pretty much. Co-ed schools were the Government run schools and while I could go there, I was told that I would never realize my full potential there.
So I went to the boys school... and I pretty much became a mess when the T started poisoning me at puberty.
I missed out on a lot of things, including girls school uniforms, dating and boys, girl scouts (I tried boy scouts, hated it) and the teen years, the malls, and maybe even my mom or aunts and cousins coaching me into womanhood.
4. SRS and surgery scares me. Maintenance post SRS also scares me with constant dilation being required to maintain what should have been a natural part of me. But it's a path I want to take.
5. Transitioning is expensive! And it's not always covered by insurance, if at all.
6. You're torn between wanting to be out and wanting to be stealth. Both have their benefits. Stealth allowing a more or less normal life, but with some fear that you'll be outed eventually. Out allows you to get rid of that fear, but some in society view you as a freak, and my fear is the "Tr***y" word being constantly thrown at me.
7. I enjoy some "guy" activities and I'm afraid of what will happen to the friends I enjoy it with when I'm fully into transition. Will I lose my friends that I go to the shooting range with? A lot of time it's just (pardon the expression) cock and balls out there. Yes, there are women who shoot, and I shoot with them sometimes but when you're with the guys it's different.
8. I am really scared of any diagnosis of mental disorder, for various reasons. Thankfully attitudes towards transgender are changing immensely and that helps.
9. Not being able to reproduce as a woman.
Things I will NOT miss:
Dysphoria (go FAR away, DO NOT come back, EVER!)
Men's clothes (boooooooring)
Health problems associated with anxiety and dysphoria
Living a lie - it's cliche but it fits
Having too hide who I am
Men's restrooms