The site is now live on Github pages. Not yet under it's eventual custom URL, very raw, very ugly (yes, I don't at all like the default theme!), and essentially no content.
But that's precisely the point. I'm an advocate of release early, so I should try and walk the talk. I am precisely trying not to overthink this, so here it goes. It's a long ways to go, but I've fixed my installation of pip, installed Pelican, created a site skeleton, and worked through the litany of settings.
The only thing I did try to think through at least a little is how I want my URLs to look. I couldn't help it - once content is on the web, I care about its URI not changing frivolously.