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I doubt a few decades of time is going to make much literature so much harder to understand. Just a little bit of historical context and background on currency values is enough to read and comprehend stuff back to Shakespeare where viewers and readers can instantly recognize the human foibles in fictional characters from centuries ago. Translations are a different beast where it’s a collaboration between translators and original author but there are many subplots in say Don Quixote that would not be out of place in media as different as It’s Always Sunny in Philadelphia to many romcom movies(I picked the oldest novel I could think of, The Iliad and Odyssey can work though translation does a lot of heavy lifting in those cases for majority of readers).
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I think one of the reasons we gave Tom Sawyer and Huck Finn to kids was because it was a story easy to relate to without the gymnastics of interpretation like we'd do with Odyssey or Illiad. I could read Hamlet and understand it as a teenager, but I didn't feel like I had anything in common with him. I wonder if the same thing is happening with Tom.
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" I just hope it isn't Katniss Everdeen or Edward Cullen."

How about Harry Potter?

Well, all of those have in common that they are fantasy and not really connected to this reality, while Tom Sawyer was a fictional adventure in reality.

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Harry Potter was published before 2000, and is upped by Diana Wynne Jones' Chrestomanci in every way.

I'd rather have one of the Baginses (not the Sackville mind you)

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What book by Jones would you recommend starting with?
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It's been ages.. Howl's Moving Castle is the most popular, and had an anime by Studio Ghibli

Normally you'd start with the first book from the Chrestomanci series, but I think The Magicians of Caprona (1980) and Witch Week (1982) might be the best for a new fan.

It's shame she passed away before writing much more and getting the fame she deserved :(

She had a unique and cozy style and way of world building and character design, where there is challenge and conflict but not deep malice or misery, if that makes sense..

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I loved Mark Twain when I was a kid. Read Tom Sawyer and Huckleberry Finn multiple times. I didn't even consider reading it to my kid when she was younger. Wasn't a good way to handle all the N words.
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Times change but people don't.
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The way people interact has definitely changed with the times. Whole plots of twentieth-century fiction and cinema would now be unlikely or impossible in the smartphone era, for instance.
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Sure, the plot devices might be rendered moot by technological change but the underlying motivations remain the same.

Technology has changed, but humans haven’t.

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I'm not sure about that, either. It's common to see Gen Z made uncomfortable by the intense flirtation and amorous pursuit shown in so much classic cinema, because that kind of sexual behavior is declining in developed countries (plausibly due to, among other factors, the ready availability of porn as a way to blow off steam, and the greater risk in the social-media age of getting one's reputation tarred if an advance proves unwelcome).
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Cultural ages of relative sexual liberation and suppression is normal too. It's a material world so yeah there are material causes, but the way people are and respond to those pressures never change because we're still the same creatures as we were hundreds of thousands of years ago.
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That feels like a broad generalization, but in either case that’s cultural. The underlying desires are still there, whether expressed or not.
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I'm struggling to imagine how that's common to see
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True. Just look at the graffiti in Pompeii and by Romans on the pyramids etc.
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I'm going out on a limb perhaps, but I think what makes people be able to relate or not is more up to the person reading the book and story, than what the book and story actually is. Sometimes me and others read the same book, both feel like we can relate to it, even if it's very old and in reality far from our reality, and we both relate to it in different ways. I'd be willing to bet that 100 years from now, people will read contemporary stories set in today and some will see nothing, others will recognize themselves somehow.
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> I wonder how many more generations we can go before that's all gone, or if it already has. There's still a lot of value in it as a work of literature, but I don't know if it has the same intuitive understanding it had in the 20th century.

...what do you think will cause kids to be unable to understand it? They understand things like the Odyssey and the Iliad, Charles Dickens, the Bible/Torah/Quran/Baghvad Gita/etc., Faust, Don Quixote, etc. all of which were written far earlier

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