Kevin, I understand a lot of the complications for attempting to set up an IndieWeb site for a static site generator like Evan. A lot of IndieWeb tech is harder to do with SSG’s since a lot of the functionality is anything but static—yet it still works. Hopefully the small handful of plugins for WordPress are much easier, particularly for someone as adept as you. I’ll admit there’s a microformats issue for dovetailing WordPress themes properly, but that should only get better with time. We could definitely use some developers and designers to help lighten the load to make it easier for everyone. Some platforms like WithKnown have it all out of the box while Drupal and WordPress have either one or a several plugins. Evan’s set up is about as complicated as they could come.
Since you mention some of your problems, a few things you might appreciate for making your own personal use easier for WordPress are the large number of Micropub clients you could be using to post to your website. They’re way easier than dealing with the Classic editor, Gutenberg, or the mobile interface. I really enjoy using Quill and Omnibear (a browser extension) myself, but for food you might enjoy Teacup and for memes there’s Kapowski. If you want a crash-course on micropub for a non-developer, I did a WordCamp session on it a while back. Since most of them are open source, I’d imagine with your experience, if necessary, you could modify them to suit your specific needs without a lot of work.
If you want to go a step further, you could set up a social reader for subscribing to and reading other sites as well as using their built in micropub functionality to reply to posts directly from your reader.
You’re right that the ecosystem does seem overly-complicated on first view, but it’s taken almost a decade of work by hundreds and thousands of people to attempt to make a set of standards that are as simple as possible for building into almost any platform out there. Further work will only serve to make things even easier and more usable over time.
Of course if one wants an easier solution (especially for the completely non-technical person who is looking for a Twitter-like replacement), there are a few IndieWeb as a Service platforms out there. One of the best I’ve seen so far is micro.blog. You can’t beat its clean interface or ease-of-use as a service and it has pretty much everything built in out of the box. As time goes by it’ll be great to see other services like this that offer the interoperability without the heartache that Evan has seen.
If you’ve got ideas about how the WordPress parts could be improved, do pass them along.