Don't worry, I understand and agree with what you say, I just found funny the contradiction between hobbies and clothing, although I understand the reasons behind it.
A very good point. Undergoing a gender change surgery is a huge commitment, like a wedding without the possibility of a divorce. How can one be sure that at 30 one will still be happy about a decision taken at 20?
An important issue is also the fact that such operations will prevent you from having children, and this must be taken into account,...
So probably the best approach is to progress gradually, and crossdressing seems a good start.