I spent a few hours tonight tinkering with WordPress. It’s different than I remember it from several years ago – imagine that!
Theming will be a challenge. I don’t want to have to write and maintain one from scratch, but if I make code changes to an existing theme (spoiler alert: I have), it makes it difficult to update the theme, which again puts me in the position to have to maintain it myself.
This is why I enjoyed the portion of customizing a theme where you can add extra CSS without having to worry about your theme overwriting your changes. Of course, you could always just make your own stylesheet and give it a name unlikely to be clobbered, such as your name (if your name is Style, I shall eat my words). I wound up using it’s inbuilt functionality.