@kashema
Good shit like this will never see the light of day in that industry.
Maybe because boys crossdressing is still seen as "mentally ill" by the anime community. (From at least the western side anyways)
Funnily enough, we can get shows centering around girls doing masculine things (example:How Heavy Are the Dumbbells You Lift?)
But we can't seem to have shows centering around where boys are doing feminine things.
Anime is full of waifu/moe blob anime girls, so I think it just always appeals to the lowest denominator.