To disagree with the post: I have always wanted to run my own servers. But for most of my time on the internet, my upload speeds have been garbage, my IP addresses have been dynamic, and my computers have been behind NATs.

The basic networking architecture during Web 1 wasn't suited to Web 1. Had it been, there might have been more people experimenting with running home servers, more work going into developing home server solutions, and thus more momentum to building that version of the web.