I went to a conventional school myself, but I had relative freedom of gender expression, growing up as a girl in the 1970s and 80s. While I didn’t realize until middle age that I was trans, I actually don’t have many regrets about being raised as a girl rather than a boy. I fear that as a boy, I would have been socialized to be more stoic and unemotional. I also would have felt less safe coming out as queer. My brown skin also would have affected how I was raised and viewed by society had I been assigned male rather than female.
All things considered, though I wish I had transitioned sooner (primarily for medical/physical reasons), I don’t think living as a young girl was a negative for me.