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).

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.

" 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.

Times change but people don't.

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.