It seems like there was more hatred directed toward gay people and now it's flipped.

There was the AIDS crisis which wiped out an entire generation of LGBT+ people and was accompanied by a major scare campaign. Since a lot of Trans people (possibly most non-closeted ones) at the time were sex workers it hit them even harder.

In the late 80s-90s things got better, to the extent that a Trans person was in some ways considered less controversial than being gay, if they were otherwise socially conforming, but the rise of "Moral Majority" types and the general right wing push towards conservative sexual mores after Clinton's shitbaggery finally managed to put an end to that.

You can see it in the change in problematic sitcom vibes from "Hahaha Male lead's best high school friend is now a hot girl, but she still loves football and beer and they get along great! Funny and heartwarming and let's not look too hard at what the writer's fetishes might be!" to "I accidentally dated a trans woman and now I might be gay, how could she trick me like that, they might trick you, the audience too! I will now nobly restrain myself from violence but still shame and humiliate the trans person! This is also not the writer's barely contained but somehow much worse fetish."