So I've gone and switched up blogging platforms again. This time, it's Jekyll. It's not that I had any problems with webby, just thought I'd try it out. After spending a few hours porting things over (mostly layout and helpers, my posts are already in markdown) I think I'm going to stick with it.
Being blog-aware is looking like a huge win - if I'm ok with my posts just being recorded by date, rather than date+time, there's a lot less overhead that needs to get done to push a new post up. I have smaller YAML preambles, and the only custom code I'm maintaining is some custom Liquid filters. With less time being spent worrying about the blog software, I might be more successful at the whole blog-writing bit. Maybe.