Honestly my main gripe with the web (and also with the Internet in general, to a certain extent) is how centralized it is, but that's an economics/people proble

Honestly my main gripe with the web (and also with the Internet in general, to a certain extent) is how centralized it is, but that's an economics/people problem, not a technological one. The overwhelming majority of Internet users don't actually want the internet, they want a portable television, and that's exactly what they got. I doubt different technological choices would have eventually lead to a significantly different arrangement, except for minor implementation details only nerds like us care about.