I think if more people would at least try to build and maintain their own website, starting with the barest of basic HTML, we'd have less of this tech wistfulness around the old web. They'd do one or more of a few things:

1) Find a personal outlet in the hand-rolled site.

2) Find that outlet, but get tired of wading through angle brackets and set up/write a static site generator.

3) Find more they want the site to do and start coding.

4) Realize they've exhausted everything they want to say to the world and abandon it.

But what else would happen in any case would be a demystification of it. Old hands would lose their nostalgia goggles, and young folks would recognize how much of the irritations of social media derived from people's dissatisfaction with the time and effort it took to shout into the void on the old web.