You make a lot of very astute observations here that I wish I were better equipped to respond to. I think there are plenty of linguistic issues involved. Words are kind of like chewing gum and tend to pick up a lot of unintended or unexpected flavors over time (see the etymology of “silly”). So not only are we at a moment where we’re working to disentangle ideas of womanhood from traditional gender roles and outdated historical norms, but also to integrate the idea of trans women. And regarding the idea of people not feeling as though they’re in the right body, idealized and photo-edited beauty standards only complicate the matter further. Sorting through the mess is no small task. Linguistically, I don’t even know if there’s universal consistency among trans women as to whether they identify as women or as trans women. It’s not clear just what kind of adjustments are going to make a definition finally “click” for us. Sort of like how changes to the Library of Congress organizational system are credited with adding legitimacy to the gay rights movement, the catalyst could come from anywhere. Or maybe things move in a completely different direction and a different classification of identity emerges.
I can’t speak with much confidence regarding overarching motivations or ideologies other than I don’t think people enjoy having an asterisk next to their identity. Most of my experience with the subject comes from my work in a high school classroom setting with a goal of helping my students to be successful. So yes, in part I’m looking to not discriminate against anyone, but also students’ individual sexual identities are largely irrelevant to my goals. If Stephanie asks to be called Stevie, it’s not all that different than if Osama asks to be called Sam. And in either case, if I’m somehow being deceived, I don’t think there are significant consequences for me. I think this also means there are a lot of conversations that I’m just not a part of given how most of my experience with members of the trans community comes from teenagers who are trying to figure themselves out and not with adults who probably have themselves figured out a bit more. I guess in a lot of ways I’m still pretty much a teenager myself when it comes to the matter.