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I really wish there were some good isekai works out there, but as a genre it's near-uniquely prone to promising really good central ideas, and then immediately dropping them for glorified wish fulfillment antics. It's not that the stories are predictable, but that where they're going is just not very interesting, and the conflict with the potential makes it really obvious. And that seems to have only gotten worse as the genre has matured.
So you have a fascinating world with deep questions... that's not going to get answered or explored. You have a character that's badly out of depth in a world where that's a punishing problem... and is going to be overpowered godmode in ten chapters. You have a relationships that have to cross massive cultural boundaries and make serious compromises... and it's not going to matter, because the main character's going to have between three and ten waifus dangling from his arm regardless of where they can even speak his language. You have an opportunity to seriously think about the portability of knowledge or critical thinking skills when entering a world where even the laws of physics are different... and it's almost always going to go full It's Magic I Don't Gotta Explain Shit.
They can be fun reads - trash can be fun, and I'm not above reading or writing power fantasy or fixit fics or harem comedy - but they're seldom deep books, and almost never good and deep. So they're trash.
Connecticut Yankee at least tries to be bitter (albeit as much to keep with the time travel stable loop thing than out of real conviction), but it's still very central an example of the genre's problems: Hank's dropped into a complicated society he deeply disagrees with, and the answer is Invent Gun and Get Lucky (both figuratively, and separately with a literal eclipse). The only real depth is using the as a metaphor for then-current problems (the aftermath of slavery, papists, the gullibility of the populace, so on), but Twain's heavy-handed enough that they're equivalent to a modern-day writer putting Ronald Grump as a isekai villain.
To be fair, Twain was also writing in the 1880s, so he was literally inventing a lot of the tools of modern literature, so it's hard to blame him too much for not reinforcing his themes with his events. But modern-day writers don't have that excuse.
Spellsinger is my personal nemesis: it opens up with an everyman protagonist who genuinely gets squicked out by the realistic conventions of a fantasy (furry-adjacent, my kryptonite!) world, along with a 'magic' that borrows from science and that the protagonist doesn't have any unique strengths with... and then there's a two-page transition that turns into the protagonist solving every problem with the power of badly-mangled rock song. It's one of the few books I've literally thrown across the room. I've read some stinkers, but this is a book that could have been a lot more.
If you want recs, RE:Zero is good if you don't mind the gore, Magic Kingdom
for SaleSold is a pretty central example of the genre and its flaws done reasonably, Vision of Escaflowne is better-known for its visuals but does a good job for its time. Dual! Parallel Trouble Adventure is decent if very much worse than Tenchi Muyo for 'stupid harem hijinks'. Dark Lord of Derkholm is kinda a deconstruction, enough that I don't really count it as isekai, but it does a good job of pointing out the problems.Ar'Kendrytheist is one of very few works to actually take its setting assumptions seriously (and finish), but it's very long and extremely progressive-coded (if only rarely so woke as to be actively detrimental rather than merely smarmy), so I'm a little cautious to put it into the clear recommend list. Arguably Beware of Chicken as a 'shorter' (aka several novella) comedy, though it's not as good about avoiding the pitfalls. I have high hopes for the Contention series, but it's just at the crux of both 'what's the answer to our grabbing mystery' and 'does the main character naturally learn from his mistakes, or does he just get overpowered' at the end of Book 2 and that's kinda the turning point between good-for-isekai and awful.
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