It's rather strange as Neopets, Gaia, College Humor, etc are sites for kids and teens that survived to the modern day in some kind of weird abstract. I wonder if there are sites like this today that will be nostalgic to the youth in a decade from now, or if the limited scope of independent sites won't result in that going forward.
Businesswise a lot of sites and franchises reset every so many decades to attract a new and younger audience, probably why so many things lately don't appeal to older generations, such as Marvel, but what's out there that's new and grabbing the next generation of brand loyalty?