(A bit of crass language, FYI, but I won't censor because the word was not censored when it was used toward me.)
I agree with you actually. These "file folders" that our brains categorize people into can be useful for us, but damaging for other people. It's why I've gotten called a "stupid
>-bleeped-<" just because I have dark skin, a big nose and curly hair. Those people don't know anything about my intelligence (I'll forgive the derogatory term because people that use words like that are just ignorant arses) but it's easy to categorize all people with dark skin, big noses and curly hair into one little folder. But like you said, this is the basis for damaging stereotypes like "stupid
>-bleeped-<" or, in our cases "feminine" or "masculine." It can be a good thing, when I was a kid, raised as a girl, I had friends because they were girls and I chose to talk to them because I could relate to them. I mean, we all had the same thing in our pants. That doesn't mean we had the same interests, but it was a start. Kind of like how a lot of us here on this site can relate because we all are actively in part of the LGBTQ community. That doesn't mean we're all going to be friends but it's kind of like one of those file folders.
Can you think about how difficult it would be to have to overly examine every stranger we met? I mean let's say I'm a straight male (I'm pansexual but I just want to make this analogy easier). If I am going to have sex with someone it is going to be someone that I am attracted to. Vagina and breasts is what it boils down to because I'm straight and I have absolutely zero interest in having sex with a man. Well, if we were in a bar looking to hook up, if feminine and masculine were obliterated, just think how hard that would be. You'd have to look at everyone objectively and think, well, can I have sex with this person? Can I be attracted to them? It's much easier to look at someone with breasts wearing a skirt and say, oh, she's a girl, I'm going to flirt with her--this has nothing to do with whether those parts of her body were there when she went through puberty but a female is a female.
If masculine or feminine things were just completely obliterated, I might as well not transition, because hell, it doesn't matter if I wear a skirt. You see what I mean?
What you see happening is actually what I think would be okay to happen--let them have "flex." I want to one day have all or at least most men not care about being read as gay. Or be able to wear a skirt. Or not take it as an insult to be called "girly." Where women aren't put off by buzzed hair or becoming muscular. A world like that would be great.
I envy the way you think, though. I am a pessimistic realist--it's really the most boring kind of person to be, ha ha. You are very right in the things you say I'm just a little more of a downer about it.