Im kinda wondering, how much of her motivation stems from being told that "girls cant do that". Its kinda framed like its the driving factor, which would be bullshit.
Well at least I'm not the only one who got that impression. It's internally consistent within the story. Looking at this page, there are hints at Chiaki's condition being more than "just" the result of socialization with utterly inflexible, prescriptive gender roles, though it's pretty safe to assume that tomboyish behaviour (and thus Chiaki's personality) had already been thoroughly judged as inappropriate by the father. Overall, however, the story gave me the impression that Chiaki wouldn't have developed gender dysphoria had "she" been accepted as a tomboy.
Given the way things developed, Chiaki did what he had to in order to have a chance at happiness, regardless of what cause we read into it.
I don't think that explains why he was so disgusted at his period or dreamed of getting his breasts removed though, it's not really a tomboy thing. I think the signs were pretty clear from him reacting to his secondary sex characteristics and sexualfunctions.
Remember what s/he say at the end of that dream "thanks Dad, now i can go hunting too" that dream clearly showed how s/he wanted to be a boy so s/he could do the things s/he wanted to do. I dont know if it was the intention or not But 'my gender restricts me from doing what i like' is at red line going through the story
You can't even call him 'he'. Stop analyzing trans people.