Octopress makes use of Jekyll and Markdown, but it's relatively easy to set up and configure. It also has a slew of plugins that add services like Google Analytics, Twitter, Disqus and so forth. Want pretty posts with nice-looking pullquotes and blockquotes? Octopress has those as well. Worried about visitors using mobile browsers? No problem. Octopress has a mobile layout that looks as good in Safari on iOS as it does on Firefox on the desktop.
Once you've set up an Octopress blog, you can deploy it to any server using Rsync or you can use it with GitHub Pages. One of the things that I find particularly compelling about Octopress is that it has excellent documentation. It seems, at least from my initial work with Octopress, that its developer (Brandon Mathis) has covered all the bases with clear and easy to follow docs from getting started to working with themes to customize the look of an Octopress-powered site.
You will, however, need to be at least passingly familiar with git and *nix command line utilities. Octopress makes static blogging easy, but it's still better suited to hackers than the marketing department or (most) editorial staff. You probably wouldn't want to spring Octopress on folks who find Microsoft Word daunting. You don't get a WYSIWYG editor or a workflow with Octopress, for instance. It might still be best suited to single-author blogs – but if that's what you're doing, Octopress should shine.
For a static site generator, Octopress looks like a winner to me. What do you think?