I loved DS9 the first time I watched it. Every re-watch I like it less and less. The first time I watched Voyager I called it quits at like season 3, then re-watched it a couple years later and it grew on me. I'm almost done with my third play-through of Voyager and I may like it better than DS9 at this point.
Same. Last rewatch was my 3rd and it was a struggle to finish after the occupation arc especially.
Happy to see I'm not alone on it.
For me, the pain starts with the election of the new Kai in those first couple seasons. But everyone else complains about the Pah Wraiths and the lounge singer hologram in the final stretch.
I actually don't know why anyone has a problem with the lounge singer, and I loved the direction they took Gul Dukat after "Waltz". My problem with the Cardassian plotline is the very end of Damar's arc:
Why DS9 fails in its central arc:
It has to do with Dukat, Damar, Marritza, the Maquis, and the two main themes of accountability and autonomy in the face of homogenization.
I think a lot of people misunderstand the turn Dukat's character took as "character assassination" when it was really just one of two directions they could have gone with his character, and they chose the one that set up a tragic parallelism with Aamin Marritza in "Duet" (which is why "Waltz" is similarly named). The whole point of Gul Dukat's character is that he never takes responsibility for his actions: the first real conversation he has with Sisko is the one where he insists that "Cardassians do not make mistakes". He's slightly off from the beginning, and it only gets more visible.
The thing that makes his character engaging is that he'll get as asymptotically close to a redemption arc as possible without ever crossing that line. The high water-mark for him is where he steals the Klingon ship and gives Kira his daughter to look after (and arguably when he helps defend the station against the Klingons). On some level he obviously wants to be amicable with the DS9 crew (and wants Sisko's respect specifically). When the Cardassian failsafes take over the station in the first season, once he's stuck with the gang he immediately seems to get kinda into helping out.
The point of him is that he's got all these redeeming qualities, but also one major flaw that winds up consuming everything else and destroying him (even to the point of literal demonic posession)—just like it did Cardassia. Marritza tried to prevent this by assuming Gul Darheel's identity and taking responsibility on behalf of all Cardassians, but that failed. Instead, Damar was supposed to be Cardassia's redemption: he's essentially Dukat's mentee and successor, but with the distinction that he's willing to own up to Cardassia's mistakes and evolve (making him Marritza's spiritual successor).
Where DS9 dropped the ball with the Cardassians was when they killed Damar. There was that whole conversation with Kira about how Damar was the kind of leader that Circassia needed, and if he had lived (and maybe if we'd even gotten to see some of what his government looked like) it would have completed his arc, as well as the point of Marritza and Dukat's. Instead, we're left assuming that Cardassia either reverted to its problems or else integrated into the Federation's broader power-bloc, killing the whole point of the Maquis.
Right, I almost forgot. Damar living and fixing Cardassia would've also been a good thematic conclusion to the Maquis arc, because in a sense the Cardassians could've succeeded where they failed: making it as a non-belligerent force in the Alpha quadrant without being absorbed by the Federation either politically or culturally (as happened to the Ferengi). All Worf could do with the Klingons was make them marginally less retarded under Martok, and the Romulans are Romulans.
But the thing is, I don't think DS9 could've
allowed itself to have Damar succeed. It was still a 1990's prog-liberal show and couldn't seriously penetrate beyond the worldview that Eddington payed lip-service to critiquing. The Klingons are the only "legitimate" essentially non-democratic state, and they're portrayed as idiots that Worf (the enlightened Federation character) has to slap around and install new leadership into. The Ferengi got it even worse. If we'd seen Bashir take down Section 31, it would've been just to prop back up the same system that led to it in the first place.
It wouldn't have allowed itself to portray Cardassia as a benign non-Federation-styled state under more virtuous leadership, suited to the Cardassian character as established in the show.
Where DS9 Succeeds the most:
Odo. Odo has the best character arc in DS9, and he's practically tied to everyone else who's also a part of his arc. The episode where he meets his foil in the other lost Changeling and figures out that Changelings are in a certain poverty because they're ignorant of sacrificial love is the best episode in the series, and it leads directly to saving the Alpha Quadrant when he shares that knowledge (along with the cure to the disease) with the Female Changeling—and Great Link, by extension. He's tied with the EMH as far as "characters who do Data's thing but better in one respect or another".
Incidentally, that Changeling definitely died of Odo's Section 31 space-AIDS unless he made it back to the Great Link in time.
Garak is Overrated:
I'd like to point out that Garak is supposed to be the best super-spy ever, but he's clearly awful at it. He's an obvious spy from the moment he's introduced. He gets outsmarted by a 10-year-old goo-child LARPing as a police officer. It seems like everyone and their mother knows about the Obsidian Order, which is supposed to be this hidden thing that's only mentioned in whispers. Sloan and Section 31 immediately make him look ridiculous. Even Eddington does, who notably did actual spy stuff on-screen. I bet you can't name 10 spy things that Garak actually did that weren't just him knowing a guy or having memorized a code his dad presumably gave him.
I like his character too, but he's clearly just a very flamboyant Cardassian man, which is already a very sassy race of people.
Why Voyager is better than DS9, taking the above into consideration:
Voyager doesn't feel like it has the same artificial internal limitations that keep DS9 from committing to the thematic conclusions of its own arcs, and doesn't have any lows as low as DS9's. There's no episodes in Voyager worse than the one where O'Brien's daughter falls into a time-cave where they re-abandon her at the end. Voyager at its worse is bizarre and sometimes boring; DS9 at its worst is embarrassing. DS9 talked about moving beyond homogenization and liberal imperialism, but Voyager actually did that without even talking about it—by being insane.
The Hirogen hologram-hunting-ships are one example of exploring a race doing its own thing in a different way and that not necessarily being a bad thing. In the episode where Neelix talks about Bankaran crime statistics and grows sympathetic toward their oppression under the Nygeans, the Bankaran who gains his sympathy actually betrays him. In Voyager, you really never can assume what's going to happen. It feels like actual exploration outside of Federation space—not just physically, but paradigmatically. In one episode you have Neelix trying to commit suicide-by transporter after going atheist in the wake of a near-death experience, and in another you have a space demon trying to get a near-death Janeway to enter his hell portal under the guise of her deceased father. Will the silver-blood clones of the Voyager crew survive long enough to reach the real Voyager? Who knows. Anything can happen. Let's have Chakotay hand a lizard-man a little globe, since we just found out the dinosaurs left earth to form a space theocracy.
And in the midst of that you have great character development for the characters that people actually want to see develop. The EMH does "becoming human" better than Data, as does Seven. Neelix goes from dating Kes to a much more age-appropriate paternalistic relationship with Naomi Wildman, who's twice Kes' age—and then, when he's not really useful on the ship anymore, he uses all the skills he got on Voyager to be the most capable man and hero-leader among the remaining Talaxians. After watching Seven develop, we get to see her mentor the Borg kids, who are great (especially Icheb). And these characters in-turn have great dynamics with the more static characters like Chakotay, Tuvok, Harry Kim, Tom Paris, and Belanna (underrated; I like how she doesn't really get along with Seven).
A show—especially a show about exploration, like Star Trek—has to be allowed to work out its own premises to their natural conclusions without artificial limits. It's not clear that Voyager is cogent enough to have limits in the first place, so it wins by accident.
Or at least that's the start of what I might argue, if I were to argue that Voyager was better.