I'm going to link to this thread in order to reply to @self-winding's latest reblog, since the thread itself is so colossal and this part of it has wandered so far off the original topic. As always, I really love self-winding's clarity and lucidity and will give them the credit for having laid out the argument in favor of transitioning as a good way to step across psychosocial boundaries which I personally find most convincing. Another way they have put it that's stuck with me for years (I think this was self-winding, or at least it was something self-winding reblogged approvingly) is paraphrased thus: gender roles are like religions in that we're not going to get rid of religion entirely, so for the moment we might as well allow some degree of laxity within religions but also let people freely convert from one religion to another.
This explanation calms my objections a lot when I squint at it the right way, although I'm not fully satisfied with it: I still would prefer to get rid of (the "believing in particular dogmas and/or that everyone should have to live in certain concrete specific ways" aspect of) religion or, if that is impossible, keep on moving towards it asymptotically (we have already come a long way!). And I think maybe letting anyone convert to a different religion for non-rationalistic "I've decided it feels nicer to believe in this other dogma and practice this other behavior" reasons arguably undermines this. The analogy becomes rather weak here -- I actually feel fine, most of the time, about people converting to a religion because the practice and culture within it makes them feel good, and have seriously considered converting to Judaism myself for such reasons although I would never take up the dogmatic beliefs of Judaism -- but the analogous statement is valid for the gender thing, I think. That is, if we want to move closer to outgrowing our societal notions of gender norms, enthusiastically encouraging as many people as possible to go through this Whole Process to switch genders in order to escape a gender role they don't like seems to undermine that.
(As a qualification, I would concede that, while I as a gnc-in-some-ways guy clearly feel threatened to some degree by this, so far, there's not too much evidence of this backwards-progress actually happening in my vicinity: I have not yet been told that I should consider that maybe I'm actually a girl because all my life I've hated sports and the mechanics of cars and have absolutely zero tolerance/ability with physical aggression and violence but enjoy fruity cocktails and musical theater and shows like Sex and the City and get really emotionally invested in relationship drama, etc. And if the cohort of self-identifying men with such characteristics is narrowing recently, I only see it narrowing very marginally.)
And one of my other arguments against it, already expressed in my last reblog to the big thread linked above, is to question whether there are actually any substantial enforced psychosocial gender norms still standing in sufficiently progressive spaces (that you want to be in anyway if you're going to transition!), apart from men not wearing dresses and a few isolated holdouts like "men by default initiate everything in a dating context" and "men don't wear make-up and women are still kind of halfway sometimes expected to". Your (self-winding's) response to that was to rightly point out that some progressive spaces (I would say what you described are some very regressive-progressive spaces) are nasty towards cis men (for being at the pinnacle of privilege) and/or cis women (for being near the pinnacle of privilege and somehow the Real Problem where social injustice is concerned) but welcoming of trans people.
But let's think about the implications of what you're saying. I remember back in the day there was a regular commenter on Ozy's blog (his handle was Zorgon and I think he was British?) who was very anti-SJ and at one point linked to a video of a very SJ-activist, completely male-presenting person who was now identifying as a woman and claiming they didn't have the resources to do any kind of physical transitioning. In the linked interview, the words they used to describe what made them realize they were a woman really really did kinda-sorta seem to indicate a man who had been beaten down by an extremely SJ-ish environment that had convinced him that manly traits are evil and who was transitioning to get out of having to belong to that hated category. At least Zorgon pointed to this as a self-evident example of a sort of "fake trans woman" in the sense of self-identifying as woman only for reasons of social capital along with social-subculture-induced self-loathing.
I don't remember much of the context or how strong Zorgon's conclusion about the trans movement as a whole was from this one example, only that my vague recollection is that Zorgon was using it as evidence of some major toxic aspect of the trans movement, and that I felt kind of icky about it at the time. I mean, I agreed with him that in this one instance, it seemed an awful lot like this person came to identify as trans for "the wrong reasons" involving social status and toxic self-loathing rather than An Actual Internal Experience Of Being A Woman, but to make out like a significant portion of trans people come to their identities that way would be... well, clearly transphobic in the same way that pointing to one example of someone gaming the welfare system as an argument against welfare is bigoted towards the poor.
But your argument about progressive subcultures that are regressive in certain ways... uh... does imply that this very thing, of coming to self-identify as a different gender not so much because of some actual truth about your gender but in order to secure social status (or from the way Ozy recently wrote, to get a pass to join Girls Shopping Day) represents some significant portion of trans people.
And I think we both, as well as many very pro-trans people, would like to see certain progressive spaces knock it off with all the nastiness towards cis men for being marinated in toxic masculinity from birth and cis women for being Karens a.k.a. The Devil, and, while I try not to judge anyone who's immersed in those spaces and just finds it too socially punishing to continue identifying as cis or whatever, it stands to reason that encouraging people in hyperprogressive spaces to transition for these reasons will implicitly appease the nastiness in those subcultures and undermine the effort to get them to knock it off.
