What were the greatest problems you faced in transitioning?

[iKate]

My issues:

Voice. Taken care of!

Beard shadow. Being taken care of!

Friends who treat me like dirt. I'm removing those people from my life.

Wife who doesn't accept. Still ongoing but we will most likely split.

Family acceptance. Mom has been very accepting as have most of my relatives. My dad is the notable exception but he can't stay mad at me forever.

Kids and religious school. I don't know yet.

Finding a suitable partner. Haven't found him yet but others give me hope.

Arrogance and other negativity within the community. For example the girl here who called me Morgan Freeman and began harassing me in PM and taunting me because she transitioned young and I didnt. Or the one who preaches  ->-bleeped-<- as if it's some sort of gospel and makes her "more trans" than others because she came out as a gay male before coming out as trans. Worse yet she claims that there should be more gatekeeping as a result. My solution? I know myself, I don't worry about people and I live my life. And the really bad harassment/hate within the community here is dealt with by the staff.

Work. Turned out to be a non issue and very accepting.

Looking like a man in a dress. I don't.

Having a "normal" family life. Can't. I guess self acceptance is the key here.

And finally, until such time as laws change in my country of birth, I will never be able to amend my birth certificate. This bothers me but I'm hoping there is a change of heart sooner or later.

Other than that my transition is going swimmingly.

[spacerace]

The cost of top surgery. The cost of a hysto will eventually also be a big hurdle.

Looking way younger than my actual age causing social complications.

Being short. Can't help that one.

I guess family acceptance will be an issue if I ever bother to contact them and tell them about it. I haven't spoken to any of them in years, but I expect they would be ashamed and not understand.

Hormones were laughably easy to start once I was ready. I ended up keeping my decade-long relationship after an initial break-up.

I live in the Pacific NW.

[KimSails]

1) My ex wife turning my daughters against me
2) My ex wife turning my daughters against me
3) My ex wife turning my daughters against me
4) State Government (Michigan, US) requiring a birth certificate change in order to change drivers license.  And birth certificate change requires notarized affidavit from an SRS surgeon.
5) The state legislature refused to vote for an LGBT non-discrimination bill unless the "T" was removed.   

99) Facial hair removal is extremely slow, time consuming and expensive.

Most other things have been easier than I expected.  I am fortunate that I live in a city that is one of the most liberal in the US and my employer includes gender identity in its non-discrimination policy.

[CosmicJoke]

I am in Pennsylvania here. I had alot of issues with expressing my feelings of discomfort within the gender role of male, and then having the physical anatomy of a male.
Getting my family to understand my need to do the transition, and that it's not some aesthetic choice.
Finding a reliable Healthcare facility was a big one. Though I found Papillon, so that was very convenient :-)
Most of my problems stemmed from communication issues with my family, and then just the general lack of understanding on their part.
I had to break away from them and start building a community that is more understanding and open to what I feel.
The school system was also like a prison sentence for someone like me.