Well, that took longer to complete than expected (as always). After experimenting with Docpad for a while I stumbled onto a number of other static site generators, finally selecting Hugo. Hugo's speed—it regenerates the whole site (all 140 pages) within ~1.5 seconds—combined with the flexible structure convinced me to give it a go.
Hugo's speediness is undoubtedly due in part to Go, as in Golang, a newer language originally developed at Google. The beauty of Hugo has been that I've not had to become a master of Golang to understand it. Hugo's templating resembles AngularJS or Handlebars in its love of double curly braces {{ .Title }}
and similar setups. Fairly intuitive, although I'm definitely still learning.
For screenshots of the site, head over here or the live site here. Update: all sites I maintain, including this one are currently using Hugo + Netlify.
Design Details
The switch from Wordpress to Hugo is a forward-looking attempt to minimize the amount of maintenance I have to do on the site, and to enable faster changes. While finishing the site took several months—working typically at most an hour a day on it—the process of iterating on the design and testing features was super quick.
Almost all of the testing took place locally, on my computer, and with Hugo's speedy page regeneration I was able to make changes very quickly, without having to debug strange bits of PHP or Javascript code in the process.
Otherwise I went straight from a super simple hand-drawn mockup of the site structure to building out a prototype HTML version within Hugo.
For a while I had the silly idea of coding all the CSS by hand, but that created resistance and getting started on that part of the project was delayed weeks because of it...then I used Skeleton as a base and everything went a billion times faster.
The bulk of designing was getting the initial layout working within the CSS, done through Stylus, and then tweaking it as needed. All done mobile-first, of course.
The one major pivot was with the grid system. Originally I used Skeleton's built-in grids, but I wasn't happy with the way it was working across the entire site, so I switched back to using Jeet, which integrates nicely with Stylus.
Deploying
What I'm particularly enjoying now is how I can push new posts and changes to the site. I still do all my writing and code locally, testing it without even necessarily needing an internet connection. Once I've finalized the new changes all I have to do is use Git to push the newest changes to the server, and a script will automatically run Hugo to regenerate the folder. Fantastic.
Future Plans
The one major downside to a static site is the lack of a search function. Right now using a Google custom search is a good work around...but Hugo now supports data files (JSON specifically), which should in theory allow for an intuitive site search that still doesn't require a database. We'll see soon(ish) enough.
All in all, while there's certainly a learning curve, I highly recommend Hugo for building a CMS-free site. While I'm enjoying Ghost for this blog, there's a distinct possibility of transitioning this to Hugo as well in the future. Futzing with logins and updates just gets in the way of writing when you're doing this solo.
Update
Yup, decided to transition this site onto Hugo as well, with a new design! In some ways less fancy than the original theme (no jQuery animation tricks added as of yet) but I like it. There's plenty of work to be done around making pagination prettier, adding some CSS animations, and gradual tweaks to typography and styling, but it's a good start.
Larger update (2019 edition)
Much has changed in terms of the plumbing of this site and my others. While all of them are still built using Hugo, since writing this I've transitioned all of my hosting to Netlify, and as part of that transition changed the build process to be based on their Victor Hugo boilerplate. As part of that transition the two major changes have been to my CSS pre-processor, from Stylus to PostCSS (I love the modularity, though sometimes getting specific plugins to function can be finnicky) and my task runner and builder from Gulp to Webpack. Overall I'm happy with the new setup, as now I can simply push changes to my git repo staged, in this case, on Bitbucket and Netlify automatically rebuilds the site each time it detects a change, plus gives me logs of errors if anything in the build process fails. So far so good, with the only significant challenge I'm finding with this method is cleanly updating the Victor Hugo boilerplate files (package.json and sometimes the webpack config) without losing my own changes to the tooling. Doesn't happen often but it does add a few hours of tinkering when it does cause issues, but that's the life of anything that relies on Node packages for functionality.