The change has been pretty dramatic in a short period of time

Emphasis on short. I know a TV channel in my country that is now known for being #woke but 10 years ago they were airing wildly homophobic content. And it was influential too, I still hear people using the homophobic catchphrases that their characters used to say. Even nowadays they still air this type of content at reruns and such.

But even this type of advance happened on thin ice. Even though a considerable part of society and media creators is being more careful regarding homophobia (and being more careful is far from meaning they never display homophobia), another large part of society is still openly homophobic and couldn't care less. And even among those who avoid being homophobic, most don't care enough to denounce the homophobia they see.

How have we arrived where we are?

Apart from the TQ+ side of woke homophobia, I think the issue is that self derogratory humor got too popular. Shows like RuPaul's Drag Race that are based on gay men mocking other gay men got too popular. Nowadays when I see gay men online, I keep seeing men that are lost in their memes, posting a nonstopping stream of homophobic content and deluding themselves by saying it's all just ironic. I see gay men that have been told that it's sacrilegious to joke about any other group, but no one ever told them to find it offensive when people make wildly homophobic jokes. I see white gay men that live on white guilt, so they can only agree when people make offensive homophobic remarks against white cis gay men. I see gay men that have bought the oppression olympics narrative, so they're unable to say anything when anyone "more oppressed" is homophobic - and they've been led to believe that anyone is more oppressed than gay men.