This is less some huge aesthetic failure and more the result of wanting your tech to feel just a little bit futuristic at all times. Over time, the definition of futuristic will change.
I understand that, though the fact that all the games are typically treated as separate entities in the same universe will hurt cohesion and the large clash between the Pokémon that blew up among kids in the 90s and the Pokémon of today is a large part of why the whole "new Pokémon suck" thing exists. It also really doesn't help that the names for these things never change (ie the PCs I referenced before are both PCs, despite one looking completely different to the other). Because of the shift in aesthetics in the world, alongside the shifts in art style and Pokémon design, people no longer recognize the franchise as what it once was, which creates confusion and irritation among the people the brand is trying to pander to with the excessive kowtowing to Kanto. It also irritates the fans by reminding them of how much the series has changed as the games continue to degrade, and creates the identity crisis I was talking about because of them trying to appeal to every single group.
They're trying to market to most people by shoving Kanto into everything because they know that's what's recognizable, while simultaneously being proud of making "bold strides" with their newer games that greatly remove the setting from what it once was to catch the praise of journalists and fans who criticized the series for not changing in the past (they've been pulling this since Alola, with the Trials, and are only being louder about it considering SV's marketing), alongside attempting to appeal to younger kids to keep the brand alive at all with greatly simplified gameplay and a lot more focus on kids through their multimedia endeavors (especially every mobile app that isn't Masters or arguably GO).
Ace Attorney is at least stuck in a courtroom setting for the most part (correct me if I'm wrong? the most I've played of it was the first two cases of the first game on DS) so very little changes outside of the occasional show of tech. Digimon is unfortunately a victim of being based on technology while also being from the fucking 90s, so it was doomed from the start lol. Pokémon is (or was) a series focused on exploring its world and raising creatures, in which you very regularly interact with tech to do so. PC boxes are called the same thing despite Kanto and Paldea having completely different-looking ones. Healers at Pokémon Centers are also deemed identical despite the newer ones having outright holographic displays while the old ones were obviously clunky boxes with very little flair to them. Pokedexes used to look encyclopedias or game consoles- they now look like or outright
are mobile phones.
These aesthetic differences don't come with any differentiation in naming, they're not given model numbers or anything, and the universe is treated the exact same.
Pokémon designs are also having the weird reverse of this problem with Paradox Pokémon being near-identical to existing Pokémon in visual aesthetic (Violet's exclusives especially) but completely different in function, while still being deemed different from their older design counterparts, which is only making the situation even more confusing.
Do you think people today wouldn't find it jarring that computers that look like they're several decades old in design would have functionality that modern computers are far, far from having?
They wouldn't, because it'd just be how they work in Pokémon. Kids probably wouldn't know that these are old computers (and if they were i'm certain they wouldn't care), older people can chuckle at the fact that they
are- they certainly wouldn't think it's "jarring". Both groups would easily get used to the iconography and just take it as a given part of the setting. By your logic, people in the 90s would've been jarred by the fact that computers in Pokémon were used for storing living creatures and video-calling (in a genuine and distracting sense, not the facetious webcomic way where "oh em gee you're digitally storing creatures in a computer isn't that weird and Totally Not Digimon Guys").
Also: re: the timeline thing, we do know the Gen 7 games are sometime past the Gen 1 games, because the protags of gen 1 are in gen 7 as adults, or at least late teens. So there'd at least be enough modernisation to bring it up to our level today.
And to throw them one more bone, there's the whole multiverse thing. Y'know, where every Pokémon game is stated to be their own universe in a multiverse, which is why, for example, you can have some hoenn adventures with Mega Evolution and some hoenn adventures without them.
That's fair enough, I forgot about that. That only applies to the Mega timeline, though, which doesn't take into account all the changes that gens 3-5 made to their own presentation that can also be blamed for this (if less-so).
Supposedly there's also a Gigantamax timeline now, too, or whatever? I haven't followed the multiversal bullshit since USUM, I just think it's really dumb and doesn't warrant being focused on ever.
None of this really matters because the games never ever mention it, outside of like two mentions of 'Fallers' in that unfinished Anabel sideplot. All these differences are never explained or acknowledged in the games, they're just taken as read.