I would say about 2-3 times a month. Mostly always out of fear if I'm choosing the right path. When it comes down to it, there is no right path. From what I've seen at least. I could live as a boy but would most likely be depressed alot. But life would be easier. I could continue on with my HRT and eventual SRS, and I "pray" that I would be making a wise but costly decision. I'm not depressed anymore, just scared. I know I will lose family along the way, and it will take a long time to be as close to being a whole woman as possible. But I've already flipped 180 degrees. Semi masculine guy, with past female relationships. To a passable quite feminine (tomboyish - thankfully) woman, and on my first relationship with a guy. So, if I looked back at what's happened over the 6 months on HRT and ask myself WTF and I doing? My answer would simply be, "finding peace within myself, feeling happy and balanced within my own body".
I feel that if I have made a mistake, in which going back to being male would be pointless, because of everything that I've been through and that has happen to my body, I would be a poor excuse for a guy.
The things I have felt and experienced within my transition so far have been worth it, if I died from doing this tomorrow, I would have no regrets. In 25 years, of dwelling over, thinking about constantly, dreaming, feeling depressed, sad, etc. I have never felt so relaxed in my mind and body then I have these last 6 months. Was it worth it..thus far? Yes..I believe so.