What I always found a bit annoying about jekyll (at least without plugin or forks) is that something like http://developmentseed.org/blog/2011/ or http://developmentseed.org/blog/2011/09/ doesn't work, i.e. the set of archive pages is pretty limited. You get one big one, and then a simple numeric pagination. I used some perl script ages ago (blosxom?), and it did just that.

Still, I guess I can hack that into the code somehow…

One "prepackaged" jekyll configuration that looks quite interesting is Octopress: http://octopress.org/