Interesting to see no one mentioned https://sandstorm.io/ yet, to really get to the small web, we would not only need each user to "serve their own site" but also buy in to self hosting other services, google docs, trello etc

Getting this right at scale is super difficult for many reasons, but the biggest one I can think of is "ease of use" for the general user, and not building things only developers or "tech savvy" users can use.