Most characters in stories suffer from the same problems current humans do. Why not write far better endings (and interludes for that matter) for all the stories? I think you are correct that we will not find the tragic tale of Romeo and Juliet anything but appalling in 100 years ("They died??!?"). So we'll probably fix them in ways that are quite satisfying to transhumans, just like we plan to fix the rest of reality. And there will almost certainly be new, better, amazing stories.
Have you read the Fun Theory sequence? That deals directly with the question of what to do with potentially boundless time and space and intelligence.
This is a thread where people can ask questions that they would ordinarily feel embarrassed for not knowing the answer to. The previous "stupid" questions thread went to over 800 comments in two and a half weeks, so I think it's time for a new one.