In a complete change of strategy, I have a new site in progress. After giving static site generators a look, as I originally thought I wanted, I decided that I really want a traditional server-rendered web site with a relational database backing store.
We do a lot with .NET MVC at work, and that's kind of what I was looking for: a framework with the flexibility to create my own content types, present them how I want, and support a way to manage the content.
After having trouble finding any kind of affordable (to me) hosting for a recent side project, I thought I'd try to stick with Dreamhost, where I'm already hosting most things. I didn't want to do PHP and Node is only supported on VPS or dedicated servers, but Ruby and Python are both available, so I looked at Ruby on Rails and Django.
I did the Django Tutorial first and was initially thrown off by the different nomenclature. Controllers are Views and Views are Templates, but mostly it made sense and the admin interface out of the box was a big plus.
So, Django it is! I'm building "in the wild" and have the first functional version already deployed. I'm working on getting these blog posts ported over right now, and then will work on getting Notes and Twitter syndication set up, pulling in my activities from Strava, and figuring something out for Instagram. I'd also like to make it look a bit nicer. There's a lot to do, and I'm enjoying the prospects before me and learning a new language and framework.