I'm not sure how old you are, but until very, very recently, transitioning was considered a drastic step and there were multiple gatekeepers in the way.
I used to read psychology books as a kid, and I remember that Gender Identity Disorder (back when they thought there was such a thing) was only diagnosed in girls as an absolute last resort. You had to be 100% masculine in everything you thought, wore, and did. I wouldn't have qualified for medical or psychological help back when I was young.
There's no point in beating yourself up over things like this. It would be great if we were all born to understanding parents in 2017, but we weren't. Even if those brick walls in the way of transition aren't necessarily there anymore, they used to be, and there's nothing that can be done about that. As others have said, try to let go of the woulda, coulda, shouldas.