I still think it will be fun in an inconsistent, man made jungle of the web sort of way. And I agree the types of mishaps are really interesting because they almost can't be replicated since they depend on so many environmental factors they almost appear physical.
There's an interview somewhere on Youtube of Bjarne Stroustroup, I think it was one of those Big Think videos. He was asked what he thought about AI and Machine learning, his response being that he's not interested in things that aren't sound.
That really stuck with me, I don't think web scraping is sound, it's guessing retrieval at broken fragments. I admired The Old Reader for including pictures in it's feed, then I saw a CNN post on there about he new M2 Macbook.....with a picture of a kitchen blender as the headline, missing the 5 or so images in the link of M2 Macbooks.