> Broadly, I think "being transgender also just a social construct that can and maybe should be addressed by loosening up our tight expectations for gender roles" vastly underestimates the scope and scale of this cultural system, the degree to which it's tangled up in our lives, and the difficulty of untangling it.

This makes sense, but I guess my question is rooted in my sense that the front that we've chosen to engage to push for re-evaluating gender is the absolute most controversial front we could have chosen. A subtler approach at re-evaluating rigid gender stereotypes—taken decades ago when we instead began to push for reassignment surgery and pronouns—could have already paid off in spades by now.

As is, the rhetoric surrounding transgender issues essentially demands that we accept that there are boxes—male and female—which people ought to be sorting themselves into, and it terrifies social conservatives because it actively encourages people to sort themselves into the boxes rather than accepting the lot they were handed. A subtler approach that started with "why shouldn't boys wear pink?" and progressed from there would have already finished the job by now, instead of creating the polarized warzone we have today. As a bonus we'd have been making life more comfortable for everyone in the middle, people who don't feel the brokenness of rigid gender norms strongly enough to want to switch entirely but still suffer from feeling the need to live up to them.

If most transgender people experience a strong biological component that demands reassignment for biological reasons, I can understand why our chosen approach was necessary. But if sufficiently changing and making flexible our expectations for what it means to be male and female would have been sufficient to make most transgender people comfortable, why did we choose the much harder sell instead?