I like this observation, and I think it is accurate, but what interests me the most is somewhat orthogonal. I remain fascinated by the difficult to admit tension within so much of trans culture, where on one hand we have some of the best perspective on the way that gender hurts, but also return time and time again to wanting gender in our lives so much, so bad.
I don't think these things actually exist in tension, except superficially. The resolution to this conflict is obvious: "Because it still hurts a lot less than the alternative." It is the answer that the classically nonbinary person lives every day, an existence staked out in a void beyond definition. All gender to them is something imposed and unwanted, yet still they interact with gender so much, more than any of us perhaps, in an effort to escape it. Bitterly, in doing so successfully their efforts invariably construct a new category of person that becomes desired by others. The world presents to all of us a bouquet of wounds, and insists we pick a few.
I remain unconvinced that transgender identity currently exists in a way that is not negative, that is not as a kind of negation. It is an ontological parasite. Requiring a notion of gender, and also a notion of desire. And desire deeply felt hurts when thwarted. I think centering trans joy, while affirming and empowering, sometimes belies that not all injuries are equal.
So much of transition and trans culture remains bound up in the negation of pain, more so than the cultivation of joy. And trying to answer the question of "Why do we do this if it hurts" from a framework centered on trans joy and fulfillment strikes me as a bit misguided. I think the question also assumes a relationship between pain and joy that is more tightly coupled than the reality. That the push and pull of them on each other is more clear-cut than it is.
When I came out, the first thing another person says to me was "Welcome to the club. It sucks, but it's better than the alternative."
And I think this tension you are witnessing is not something inherent to transgender identity, but rather a change in dominant narratives. Trans joy is, culturally at large, only a very recent possibility. Not just pride but simple happiness at not having to go through the wrong adolescence is a recent thing. And some part of me dares to hope that "Why do we come back to the things that hurt us so much over and over" will turn into "Actually it doesn't really hurt us at all anymore" for the younger generation.
There is a question to what degree can you extricate transgender as a category from gender itself; would you have trans people in a post-gender world? Would there be a trans femininity without patriarchy, which after all is what defines femininity as we understand it?
This always struck me as a bit of a strange question. But it's one that also gnaws at me because my relationship to my own transition seems very divorced from the transgender community's at large. This is because my transition...wasn't in so many ways. That is, my transition consisted of changing my name, taking HRT until I male-failed, and then getting FFS.
I almost never use the changed name, everyone calls me by a gender neutral nickname at this point.
And this all circles around a strange question that bounces around in my brain sometimes:
"If your transition had gone the same but everyone still treated you as if you were a male, would you still have gone through it?"
The answer of course, is a resounding yes. I transitioned because of a bone deep conviction that my body was wrong. One that had hounded me for my entire life. And I find myself, because of the materially rooted nature of my dysphoria, in the unenviable position of being "One of the Good Ones." The "understandable trans person who checks all the gatekeeping boxes." And it actually kind of sucks because a lot of discourse in this community basically proceeds under the assumption that people like me don't exist, or worse, that we're transmedicalists. For me transition has always been about the simple alleviation of pain. Good never entered into it, though I've always been a grim creature.
But I think the answer to your question is potentially: yes. I think that there will always be people who look at secondary sexual characteristics of specific types and go "I would like those instead of the ones I will get without intervention and I am very willing to suffer to get them." The rub here is that if you go with this, is that necessarily a post-gender society? Because as an answer goes, it's kind of boring! It presumes that people will always naturally group others by tangible sexual secondary characteristics in a way that sidesteps substantive theoretical considerations. And is circular in the sense that "How do you know what a wo/man's body is supposed to look like outside of socially constructed contexts?"
I do feel though that this points us towards a more generalized notion of transness. One that can encapsulate future ideas of trans identity, potentially even far flung science-fictional potentialities. That being trans may be reformulated as "normatively transgressive expressions of morphological freedom." Unfortunately this seems like another side-step, we've solved the problem by lopping the "gender" off transgender. But it does highlight an important an issue I think that also points at a latent tension in the queer community right now:
Does the ideal post-gender society have the free proliferation of perfectly permeable gender categories or has it abolished them altogether? Can these be the same thing? Neopronouns currently remain unpopular, but they point at a sort of need to be liminal and indefinite that for some people appears to be a very real thing. I am beginning to believe that humanity will always have a tendency to strive towards some ineffable outside, to inhabit the strange and expand beyond categories. While at the same time, there will be other people driven to categorize and nail down everything around them, and they will always exist in tension.
Honestly, it's quite charming.
But I suspect what would happen in a post-gender society where it has all been abolished is this, a thing we see the precursor of now with catgirls, dog-girls, demongirls, and on the opposite end-tradwives. We can see a broader trend towards aesthetics taking the place of gender, and gender being rendered as a kind of aesthetic presentation. And if our post-gender society looks like that well, one could conceivably argue that the transitional state where an aesthetic is primarily aspirational as opposed to something recognized immediately and intuitively by others not yourself would be the analogous "transgender state."
I don't know, I find myself running in circles, but these is the first time I've ever had the chance to put some of these thoughts into words so I'm taking them, even if this is a bit of a ramble.