I am enjoying this part of the discussion. One of the things that struck me a few years ago was how the design of the web was so heavily oriented around trying to reproduce the print media industry in a browser. Thus, we get the "markup" of HTML, which provides layout at the expense of structure. Later on, we added CSS which ideally should provide layout, but bad habits learned at an early age or provided by tools that came about in the 90s still haven't caught up in many cases to this day.

There's no concept of "line 4 of chapter 3 of book X" in the web, at least not down at its core. You have to shim it in with anchor tags or something similar, and as a result we don't have ubiquitous browser apps that let me highlight a snippet of text in a book, write some notes in the margin (example: "this is a reference to Hamlet's soliloquy"), and then on a whim search for all of Noam Chomsky's (or whoever's) notes on Hamlet, or perhaps search for all public notes on this book in the context of Hamlet. The lack of structure means that everything's this haphazard soup of markup, with the focus being so much on how it looks that structure of the text and the relationship between parts gets lost. I'm not sure the "semantic web" will make up for that lack, but it's probably a good example of how the "next web will be built on the bones of this one" (to paraphrase someone else's comment in this thread).