This set is a big fat nothing, overall. The ideas going on aren't inherrently bad, for the most part, but it's mostly one bit of missed potential after another.
Battle 16
Star Trek 3 and 4 reference in the location. Sure, why not? - Dave being mad about the records being wiped in the version restart at the start is amusing but probably ends too soon to really work.
Characters sometimes reading Sandy is definitely a cute running gag that I was able to do in classic but the way I've set up modern isn't viable. The joke about Dave assuming the Devil to be male is... Fine, but doesn't really go anywhere.
And then we wind up with the core of the battle, a surface level Weakest Link parody. Now, yes, as some - even at the time, even within my age group - were pointing out - rightly pointed out, the obsession with 'Anne Robinson is evil' as humour doesn't really work since she's so obviously playing a character while hosting the show (In fact, that character was apparently conceived in response to the pilot where she was apparently the normal 'neutral arbitrator' role of a host of a 'serious' quiz, and due to the nature of the format the contestants started getting nasty towards each other, which lead the format developers to lean into the nastiness. And while that worked for Weakest Link it often didn't for the various copycats). But the idea of dialling up the nastiness and using Robinson as the face of the show whose success lead to a trend in gameshows for nastiness to represent and exaggerate that trend just makes a ton of sense. (The version of the joke made within my peer group at school was 'Weakest Link where Robbinson's armed with a gun' around 5 years before Doctor Who made ostensibly the same joke in the first season of its revived run, albeit playing it for drama rather than comedy). This Battle was written in 2001, so still just a year or so out from the show's premiere.
The problem is... Well, this battle just doesn't do anything with its premise. There's a much funnier version of the battle which exaggerates the nastiness of the show while forcing Dave to participate in a round or two, rather than the 'oh isn't Anne Robbinson a bit nasty on the show' as the only real joke of the actual battle. Cute reference to the All Your Base meme as Dave escapes the Narrator rehearsing rhyming schemes, at least. Cute ideas, but none of them feel fleshed out enough.
Battle 17
The Narrator and SVWebmaster talking shop is something I enjoy about classic Sandy. The joke about Dave getting used to the Narrator making him less fun to torment is cute. And I think this is the birth of the Sandy lacks trees, and instead having palm trees gag. Though I tend to imagine the fronds of a Sandy Palm Tree being giant green hands these days rather than as described here of 'a tree, with hands.'
As for the bulk of the Battle - This is, I think, my first attempt to make a silent protagonist work in the context of PokéBattles, something that would eventually lead me to create Emojiman.
...And then I actually succeeded with the vanilla version of it with the first battle in modern Sandy where Red's the player which was written that way out of the necessity of Red being the player for that Battle and somehow it just worked a lot better than this attempt did (Though this attempt isn't nearly as painful to read as I edit it into my head as being when thinking back to it)
Battle 18
I think the biggest problem with this battle is that it's utterly, completely, toothless. It's political comedy with absolutely nothing to say. Which, considering what passes for political comedy in some circles these days, isn't the worst thing in the world, I suppose. (For the record, the leader of the Lib Dems when the battle was written was Charles Kennedy, and the leader of the Monster Raving Loony Party was Howling Laud Hope and his cat, Catmando.)
As for what passes for substance in this battle, joking about the water quality of Blackpool's beaches is fairly timeless, the idea of holding an election via Yahoo Groups is... Horrific, but also a funny concept... And this battle introduces the Emergency Narrational Hologram, which... Would go on to have a lot of significance later, though here is mostly just a Star Trek Voyager reference.
Battle 19
...Oh god the reference back in Battle 16 and 17 to a poetic battle was serious. This battle wasn't a horrible fever dream of mine. The biggest issue here is that it's all rhyming couplets with absolutely zero sense of rhythmic flow. Now, formalism isn't the most important thing in poetry, and going as far as Iambic Pentameter or whatever would have been overkill, but with just the rhyming couplets I'm not sure the gimmick really works for the battle.
...Saying that, while nothing in here is what I'd call good, the rambling style Sandy sometimes lands up in actually helps it - It just keeps going and that has a comedic value of its own, in a way. I wouldn't call this good today, but it definitely flows. The post-battle scene is entirely a reference to the IRC channel of the time. The internet was a very different place in 2001 is all I can say about that.
Battle 20
...Let's ignore the character assassination of Deb for a second here, and just focus on how few jokes there are in this battle. Saying that it's appropriately cute as a battle about Kawaii goes. It's also one of the battles where the tiny frame for text in this layout really doesn't work for.