My biggest problem had to be fear - I'm scared of calling people on the phone and of making appointments, for goodness sake. I was terrified of losing everyone, of losing my job, of having to deal with doctors, of medication... I was basically scared to death for a year. On the other hand, I was fortunate enough that my wife handled all the finances, and we shelled out probably $28K for my entire transition.
(Francis Ann : Don't panic about GRS! Brassard is one of the more "conservative" surgeons when it comes to depth creation, and even he didn't have to resort to skin grafts until he had a woman who was less than 2" erect. It's truly amazing what they can do now, and it's NOT going to be as precise as "what length you have is your future depth," even though they talk about inversion and whatnot.)