Agreed.
I'm not suggesting there ever was and Edenic period where things were easy, but I do think an argument could be made that things have gotten worse for the non-technical beginner looking to host their own site.
First, they've got to make a decision of which publishing platform to install on their site. They'll probably see some online debates, talking about static site generators vs Wordpress, etc. They'll waste a few hours trying to figure out what choice to make. Once that decision is made, it's next time to find and install a better looking theme, because no platform seems capable of looking decent enough out of the box.
Compare this to handwriting and uploading html files, and it seems like we've gone backwards.
> the reality is that most people... do not care about high quality publishing or readability
I'd argue the opposite. Empires of platforms have been built around being high quality and easily readable. Look at medium, and look at instagram. A slightly better publishing experience dominates.
And to further that note, how would you self host a photo site for mobile? Is that even possible? How would you begin?
What if you wanted to make a self hosted snapchat type site for your friends to see your photos?
I've made a few unfair points, but I think the general idea remains, the self publishing tools haven't kept up with the rest of technology, in general.