I've been growing out my hair for about a while now, and always hate the idea of getting it trimmed because there are so many things I'd like to try with it that only work if I have enough hair. So I relate to the trimming trauma. On the other hand, you need to keep the split ends under control and the shape flattering whether you're in guy or girl mode. So there's that to think about.
Anyway, I've mostly just brushed off the comments about my hair when in guy mode. I found that once it got long enough to pull back into a ponytail not many people really noticed any more.
My issue has been clothes. I hate putting on feminine clothes over a body that still looks WAY too masculine to me. I feel like a fool, and an ugly one at that. But there will come a day when I'm ready, and at that time I don't think I'll have several thousand dollars in spare cash to blow on a new wardrobe. Besides, I need actual practice going out and trying to pass well before I'm "perfect" in my mind.
So in a way, yes, I can relate to getting all upset about minor stuff. I try to keep my thoughts on the long term whenever that stuff tries to bring me down. That seems to help.