Jekyll In 15 Minutes
benhowdle.im
benhowdle.im
A couple things that might have been helpful would be to mention how to create new posts (since they have a specific format) and perhaps linking to a barebones deployment of Jekyll that followed along with your post (though you did link to your site, so kudos for that).
Keep on writing. A Jekyll plugin tutorial (as mentioned by ElongatedTowel) would indeed be a useful resource.
The thing that kind of blows about Jekyll is you kind of need the local Jekyll environment to build your site. I kind of am starting to get to a point where I want to be able to have some hybrid of a web interface and local dev. Something like using Github's distraction free writing to create the pages, then be able to publish without the local setup.
I guess I should just put a jekyll server in the cloud somewhere...
I guess if what Jekyll or Octopress provides out of the box they are the best choice at the moment. At least that's probably why they are so incredibly popular.
I started writing my own solution but I realized once you get past a certain point it's actually pretty hard to design something like this. And with the amount of static site generators out there it wouldn't ever have a chance to compete no matter how good it would be.
I wish it was easy to just replace the Liquid templates completely. No template inheritance irks me the most.