I'd start with Strange New Worlds. It's very classic Trek in terms of its themes and stories, but as it's still being made it has contemporary audiences in mind. If you like it, I would then go to TNG.
Yeah, you're right about the footnotes. I read someone the other day saying they felt like Kuang was writing with an imaginary social justice scold hovering over her, and I think that's about right. I find it odd that someone feels they have to say 'racism — which is bad, by the way — exists in this society'. We know it's bad! Even racists don't like being called racist!
Only three, huh? And people say he can't change.