If you think of hypertext as a medium, it's been pushed to its most logical extreme already. There's not a lot of boundaries to explore.
There are weird places online already, sure. And curiosities still abound. But idk… I wonder if a generation lost in cyberspace is exactly the reason why we are actually so unhappy with the internet writ large.
Nostalgia is a hell of a drug.
I think this is an odd framing. It's not about pushing things to further extremes, it's about using all these mediums that have been allowed to wither and die. It's about getting out of the sterile high-walled gardens.
Let's take LiveJournal or MySpace… those services arose out of an interesting time when the metaphor of daily posting on the web was novel to a lot of people. Sharing photos on the web was novel so Flickr was created. During these times, folks are figuring out the design patterns of the web that get crafted in HTML/CSS/JS and now they've all but been standardized and commodified by Meta et al.