I think I'm in the same boat. I remember having conversations with my wife around 2015 about being somewhat frustrated about trans people's pronouns and wishing there was a better way to refer to them. I was very much in the "I don't care what they do" mindset like you mentioned. Looking back is so wierd. At the time I sort of considered myself a libertarian but didn't really get involved with politics. That changed so quickly with Trump (and specifically the United the Right rally). It really made me more politically aware. Anyways, like you I started watching ContraPoints. I think a friend recommended the "how to spot a fascist" video. It's hard to say if her content really had any effect on me becoming more trans-supportive than trans-tolerant (like you said) or if it was just a natural progression for me mulling stuff over in my brain over time. I look back on that conversation now and cringe. It wasn't outright transphobic but I'd definitely consider it a yellow flag hearing it from someone now.