I see David has given this a lot of thought
I know my movie preferences have fluctuated a bit, except for my top 3 and bottom 2. I always have TMP, TWOK and First Contact as my top 3 in that order. My bottom two have always been Insurrection then TFF in last place. Though I always add I don't hate any of the movies. I can watch TFF and have a good time watching it.
My middle films tend to fluctuate. As time has gone on I've actually dropped TUC and Star Trek (2009) a notch or two. I loved both films when they came out, but neither has aged as well for me. For some reason each time I watch Star Trek (2009) I like it a little less. It's just not holding up as much for me.
But then, I'm a bit out there. TMP is my favorite Trek film, which is a bit unusual, Beyond is my favorite Kelvin film and I liked Nemesis--to this day I don't understand the hate that movie gets. I mean it's not a masterpiece of science fiction, it has its flaws, but I really don't understand why so many people seem to hate it.
I'm not surprised the original series ranks at the top of many lists. There's just something fun and pure (from a Star Trek perspective) about it, I guess because it was the first. Hell, I even get a kick out of "Spock's Brain" despite how ridiculous the entire premise is. I agree with David Mack that DS9 was a great series, definitely top 3. When it started I wasn't so sure. A Star Trek show on a space station. But it really turned out to be one of the best sci-fi shows out there. I loved the Dominion as adversaries too. The Borg are a great villain, but by their very nature there is only so much you can do with them. The Dominion is far more versatile as a villain. And, well, Gul Dukat--a huge amount of credit goes to Marc Alaimo on that--equal parts evil, creepy and charismatic. And all the twists and turns. Ditto for Garak, another great job by Robinson in that case. They had a great cast and supporting cast, probably the best of all the series. As goofy as they can be, I even enjoyed the Quark episodes.
Honestly, though, I've never come across any Star Trek that I actually hate, though I have to admit Enterprise's finale, TATV comes perilously close.
As for the new Kurtzman series? I'm still considering those I think. There are things I liked about Discovery and Picard, and things I'm not sure about. But I'm trying to keep an open mind. See where they go. I'm currently watching the first season of Lower Decks for the first time. I'm having a hard time getting into that series. I expected it to be different, looser and more comical. But I'm about halfway through and the funny parts aren't as funny as I thought they'd be and the stories themselves aren't really grabbing me. But we'll see. I don't hate it, I'm just having a hard time getting into it.