Let's compare modern blogging to how you would have blogged in 1996, or when Berners-Lee launched the first documents at CERN, your workflow looked like 'write .html file, FTP to server, Apache serves static files to anyone who visits'. In 2016, your workflow, if you want to, looks like... 'write .html file, SCP to server, nginx serves static files to anyone who visits'. You can still write HTML5 by hand, it's not harder than original HTML (may be easier). You can write Markdown which compiles to HTML with no more fuss than 'markdown.pl foo.md foo.html' or 'pandoc foo.md -o foo.html'.
You don't want to run a server? That's fine, find a host like S3 and instead of 'scp', 's3cmd'. It'll cost you next to nothing compared to back then.
You want some sort of blog software? There must be a million which are not named 'Wordpress' and do not have endless security nightmares. You want static site generators? Likewise, millions. WSIYWG HTML editors? Likewise. Free hosting? At this point almost any large site offers blog-like functionality because hosting is so cheap.
But what is harder? If you want to run your own server, everything is infinitely easy than in 1996. Apt-get may or may not have existed in 1996, but I'm sure it was far less comprehensive and reliable than it is now. You can let your server run for many years without upgrading if you want, and when you do upgrade, it's a few commands. Why, you don't even need to compile a kernel or buy a server edition of your OS. It has never been easier nor cheaper to run your own website in a myriad of different methods. So what exactly has gotten 'so damn complicated'?
The reality is that most people, and especially casuals, do not care that much about high-quality publishing or control or reliability, and instead care more about extreme convenience and network effects, and often either have nothing to say or don't want to say it and so no matter how polished your static site generator is, they couldn't care less. As Yogi Berra said, "if people don't want to go to the ballpark, how are you going stop'em?"