Regarding point 1, Roddenberry was indeed very open about his desire to make sure that when people watched Trek, they saw a version of the future where things were more egalitarian. He wanted a woman to the first officer on the ship, even though he also had Pike voice some consternation about having a woman on the bridge regarding yeoman Colt. He wanted people of colour on the ship. During the height of the Cold War, he wanted a proud Russian character on the ship, and even made up a story about being a Russian magazine article criticizing the lack of representation. He wanted people of colour on the ship. According to George Takei, when he tried to convince Roddenberry to include gay representation, Gene said that he wanted to, but couldn't push for that with the studio. TOS famously had the first scripted interracial kiss in a North American television show.

As you alluded, even if we recognize that some of Roddenberry's motivations were money and ratings oriented -- like having Chekov's hair be styled like the Monkees' to appeal to a younger demographic, or his introducing the Vulcan IDIC he could sell merch of it -- we also have to acknowledge that he was dedicated to portraying that egalitarian future as much as he could given the constraints of the era.

But how do you know the motivations of the people making those decisions today?

I never said I doubted Roddenberry’s intentions. I don’t particularly doubt the modern team’s, either, though.

Representation that cares about the issues tends to be more honest and true than the tokenism and hand-puppet waving that more typically come from targeting a consumer audience.

That sounds fair to say in general, but it’s not very specific. Which characters in modern Trek would you say are token minorities?

Ah a clever and biting retort to be sure! A short and sweet dagger to the heart of the argument. Your college debate team is clearly very lucky to have someone like you among their ranks! However, I warn you, the fediverse, my friend, is the biggest of the big leagues, and such concise witticisms and stinging flashes of showmanship will not suffice to pull your seemingly iron clad observation across the finish line! Tokenism is not representation.

As opposed to characters walking around modern day San Francisco discussing environmentalist taking points while literally trying to de-extinct an at-risk species?

Please. Trek has never been subtle. Anyone accusing Trek of "trying to be too woke" were never paying attention in the first place.

It's so crazy how the difference between "preached" and "commented" is based on your specific opinion of where social progress should have stopped 🤔

That's a potentially valid complaint, I was thinking more of people just complaining that Star Trek is bad just because it's become too woke and liberal, though. People like my father will just moan, "I don't know why they have to make it political with this stuff, Star Trek never used to do that." if he sees an episode with more than one black character in it. There are some real idiots out there.