I read someone's review and I agreed that it played out like a poorly written porno/hentai more than anything.
I get what you're saying about Woke Up as a Girl but I feel like that's basically what we get?
It's kind of clumsy to go "oh, if you're a woman, sit there and cry, but if you're a man, go out and get her", but I think Toshihide's personality was more of a "flaw" rather than a "diversity".
He'd sit there and cry and if nobody saved him, he'd just curl up and die. I don't think that's something that should be encouraged, no matter your gender.
In addition, the short ends with him crying because he's a soft-hearted person in his core, it's not like he does a 180. He's still a softie with his domineering girlfriend.
I do agree that it's a clumsy way to handle gender dysphoria (as much as a cis man can speak on that issue, anyway) but it felt more like a shell through which to get Toshihide to develop and grow as a person.
I mean it wasn't that bad but like its all so predictable and nothing really happens through the duration of it. The ending was kinda weird but still i just enjoyed the artwork the most.