Season 5 pulls the ripcord on the Dominion plot, and manages to do so in a way that incorporates the other threads developed over previous season rather than abandon them. If nothing else, that puts the season on pretty strong footing. It's not a perfect season, and there are definitely still some stinkers, but I think it's safe to say that if you are trying to convince a friend, Trekkie or not, to give DS9 another shot, you could do far worse than a sampler box from this season.
The best scene of the season was the final scene of the Kira-Odo relationship. Oh, wait...
Much like the two-parter involving the dominion is Season 3, "Improbable Cause" and "Die is Cast," the Dominion two-parter in this season, "In Purgatory's Shadow" and "By Inferno's Light" really ramp up the season and the series for me. I think a common thread of the really good episodes over the course of this series, and the idea that will define the later seasons' serialized stories is just the sheer amount of stuff going on while not feeling out of control. Taking the two-parter for example. You get Tain, Garak, Dukat, Secret Bashir, Ziyal, Love, Betrayal, Plotting, More Plotting, Worf, Fist fights, Martok's alive!, and somehow, rather than feel like they were just throwing ideas at the wall, the hand at the wheel is steady, and the chaos builds rather than crumbles. Whatever our other problems with the season finale, I think you can say the same thing. A ton of shit just happens at a breakneck pace, and again, rather than feel jumbled, it just feels intense.
This is the long way of pointing out a basic difference between TNG and DS9, when it's good. TNG was about characters involved in little morality plays and watching those characters adapt and change. DS9, for better for worse, is less about the characters, and more about the sweep of events. Rather than being the centerpiece for the story, they are caught in the current and have to keep up. The result is, finally, a distinct flavor of Star Trek that is DS9's own. On the one hand, I don't think even the most ardent DS9 fan could argue we get close to sense of family and community we got on the Enterprise, but I think in exchange, when all the cylinders are firing, a story that is gripping on a week to week basis in a way that TNG wasn't. Letting themselves finally do that full bore gives the show some of its most successful episodes and arcs.
Something you've said above makes me think. This would probably be a good first season for someone to watch at least a good half of. Is that because there aren't good episodes in prior seasons? No. But this is the first season where various episodes feel essential in the same way that BoBW or Yesterday's Enterprise or The Pegasus felt in TNG. Which is really just a way of saying that DS9 didn't seem to know what the hell to do with itself in seasons 1-4. It seems like they kept wanting to build this or that character relationship, complicate things, inject romance... and I just didn't care. Kira and Shakaar? GMAFB. For various reasons, these characters simply aren't as interesting or engaging as those in TNG or TOS. But the best of the episodes in the prior 4 seasons have been when the setting they've created actually gets explored in a deep and meaningful way. Here, especially in the multi-part stories as you say, characters take a bit of a back seat to the events. This is a good thing.
In this season, the backdrop of the Federation, the impending war with the Dominion, and the shifting political tides on Bajor, actually eclipse the general level of interest in the backdrop of the prior series. That's really saying something. So now, where lackluster characters had held back the show previously, things are really fun to watch.
I am sorry to sound as if I'm damning with faint praise. I'm trying not to. There have been good character stories in prior seasons. Sisko's relationship with his son is pretty good story fodder. Quark's "otherness" in comparison with those Federation citizens surrounding him is always interesting. Garak and his mysterious past. Nog's desire to fit in. These are good bases for stories. But TNG especially excelled at making sure every character had an interesting bio, growth to go through, and so on. Bashir had to have it grafted on via retcon in this season. Chief O'Brien will get his soon enough. The bazillion-and-one Dax hosts have rarely been interesting to me. Kira is hampered by only really having one story thread (yes, we get it, she was a rebel). Nothing here is as easily identifiable and relatable as "formerly ambitious guy finds his comfort zone" or "man carrying a torch for married friend" or "wunderkind wrestles with expectations."
Kevin: Well, I can't say enough good things about "In Purgatory's Shadow" and "By Inferno's Light." That moment when Kira realizes Dukat has betrayed, well... everyone, is just great, and it gives me goosebumps a decade later. I remember thinking about both the personal sense of betrayal and the broad sweep of intergalactic politics all at once. And again, whatever flaws the episode may have, it was never for a moment boring.
"Trials and Tribbleations" is an episode that doesn't have to exist, sure. It was done more as a proof of concept for the next generation (hehe) of computer graphics. That being said, if you can't like that episode at least a little, you might not have a soul. Watching Terry Farrell swan around in gogo boots and gush about 23rd Century design is one of the most charming moments in the franchise. All the jokes land, and unlike other trips to other series (looking at you Enterprise finale) it in no way damages the source material.
"Rapture" was an unexpected highlight. Somehow two things that tend earn our ire here, boring Bajoran politics and Avery Brooks speechifying, combined to make a seriously good episode that gave Bajoran politics and religion some actual heft and consequence.
Lastly, "Ties of Blood and Water" remains a personal favorite. It really shows off how much Visitor has grown as an actress, and that last scene still kills me.
Matthew: My favorite part of the Purgatory/Inferno story was the Worf bit fighting the Jem'Hadar. It was a great encapsulation of why Worf can be really cool - he represents the potential bad-ass-ery of the Trek universe, but in a Starfleet way, trying to adapt his culture to the culture of humanity at large. Now, to be sure, this is later undercut by "Let He Who is Without Sin...," but whatever. Add in a great Garak sidebar and a long-awaited advancement of the Dominion storyline, and you've got a winner.
I think "In the Cards" represents the DS9 cast at its most likeable, and the comedy writing at its sharpest. Even better was that it worked in a story thread that advanced the overall plot of the show. This was a story that showed us the other side of "The Visitor," the lengths to which Jake will go to make his dad happy. Sweet and funny.
"Nor the Battle To The Strong" is a nice preview of some of the tonally different war storytelling we'll get next season. In its own right, it's a nice look at how someone as pampered as a Federation citizen might react when thrown into a warzone.
Kevin: The master copy of "Let He Who Is Without Sin..." should be launched into the sun. Aside from being a tepid, cowardly mess on the subject of sex, it puts the nail in the coffin of Worf being a jerk.
I enjoy several moments in "Ferengi Love Songs" because I like the actors and they can almost carry anything you hand them, but still...not a good episode. Note to all Star Trek writers: Take a page from the Golden Girls. Old people's sex lives can be funny, but only if you don't treat the mere idea of them having one as stupid. It's a lesson you missed more often than not with Lwaxana Troi. The Ferengi, when done well, have one of the best shots to use science fiction's mirror on humanity, but when you miss the fairway this badly, it becomes varying degrees of unwatchable.
Matthew: Normally, we don't talk about the same episodes in this section. But for "Let He..." we have to make an exception. In addition to being a horrendous episode for many reasons, some of which you mentioned (weak-ass portrayal of future sexual mores, terrible production values, unbelievable antagonists), it assassinates Worf's character. He goes from being an interesting, nuanced guy in TNG to being a controlling, borderline abusive dickwad towards Dax here. Add a gratuitous retcon (killing a soccer chum as a child) and you have an utter abomination. Michael Dorn should get one free face punch on every writer and editor involved in creating this.
"For The Uniform" starts out as a boring follow-up to a boring storyline - Michael Eddington as traitor. But it goes off the rails in spectacular fashion when Sisko obliterates all life on a planet in order to get the Maquis to acquiesce, doesn't even receive a batted eyelash from his crew, and then suffers no consequences. Complete trash.
Kevin: Again, I'm a little surprised by the actual numbers. My internal sense of the show is always that each season is better than the last, but this comes in a fair bit behind season 4. It's still a good season, and better than any other but Season 4 of DS9. I think what holds it back is the lack of a ten. I may disagree with Matt's 4s for the two-parter, but I can certainly see his point, and that's not something you could have said about the best of TNG's 5th season. Also, there are more missteps here than at the same point in TNG's life. It's not entirely fair to make direct comparisons, but I think it is worth pointing out that the problems with Let He Who Is Without Sin should have been obvious to a new staff, let alone the experienced one that made it.
And now for charts:
Matthew: Having just watched Season 7 of TNG on Blu-Ray, it doesn't surprise me at all that this season squeaks past it. There is a lot more narrative momentum and verve here, even if there are some stinkers intermingled with the better shows. TNG S7 had a somewhat "tired" feeling overall (keeping in mind that I'd still rather watch it than almost anything else).
I was worried that I was being harsh on this season for various new-baby-related sleep deprivation reasons, but seeing my stats, I like the look of my bell curve.
Kevin: A few missteps still hold the show back overall, but I think its safe to say the show has left behind boring stories, and I think they really should be commended for their ability to throw a dozen plot elements at you and not have it feel lazy, but orchestrated. They have, at the very least, learned what they are good at, and seem to be inclined to keep doing it. Like I was the summer it aired, I can't wait to get back for season 6 in a few months to pick this story back up.