After thinking about it for some time, I finally made the switch to Hakyll. I've been learning Haskell for the past several months, and after getting annoyed with how often Jekyll and Octopress broke (every time I tried to update them), this seemed like a logical move.
Moving things over to Hakyll wasn't really all that hard, since it has support for the awesome Pandoc library. This meant that all of my markdown from Jekyll would easily port over (with a few changes to the metadata fields, which were accomplished with codemod).
Overall, I really like Hakyll so far. My site.hs file is barely over 100 lines and for the time being does everything I want. Hakyll even handles tags and pagination, and can handle calling out to other system utilties, process assets such as sass/scss or Roy scripts.
The last thing I wanted to do before calling my migration done was set up some redirects. In the past, I had two Jekyll instances, one for my blog, and one for my personal site. With this migration, I merged them into one Hakyll site. So I needed to redirect old links from "blog.elrod.me" to "elrod.me".
Hakyll, by default, exports things with slightly different filenames than Jekyll/Octopress. Instead of "/blog/2013/12/29/post-name/index.html", Hakyll uses "/posts/2013-12-29-post-name.html".
Both of these are very similar, and doing a simple rewrite was all I needed. So I created a new VirtualHost on my server, for the old subdomain, and came up with this:
<VirtualHost *:80> ServerName blog.elrod.me RewriteEngine on RewriteRule ^/blog/(\d+)/(\d+)/(\d+)/(.+)/$ http://elrod.me/posts/$1-$2-$3-$4.html [R] RewriteRule ^/blog/(\d+)/(\d+)/(\d+)/(.+)$ http://elrod.me/posts/$1-$2-$3-$4.html [R] Redirect / http://elrod.me/ </VirtualHost>
...which doesn't cover every page on the old site, but at least redirects the old blog post URLs.