Almost every Stephen King book with an unhappy ending! :)
For example: >! I loved Firestarter! But so many of the main characters died horrific deaths, that it’s hard to reread, knowing what will happen! !<
Similar with >! Christine. It’s well-written, but the main character dies in the end, and again, it’s hard to re-read, knowing what will happen !<
Also >! Under the Dome. Everyone dies, making the struggles during the book seem pointless. (I know that was kind of the point of the story! :). But then it makes it hard to reread, knowing that. !<
Depends on the circumstances.
The book “Are you there God? It’s me, Margaret” had references to “sanity belts” for your period, which just confuses younger readers! Those haven’t been used in decades! So that’s fine.
But adding cell phones to “The Baby Sitters Club” is silly. Especially since it would’ve made it unnecessary to gather at Claudia’s house to dole out babysitting jobs!