Regarding our blog, Reefpoints (http://reefpoints.dockyard.com/), all employees are encouraged to publish articles. We have designers, developers and project managers writing about technology, design and process. Moreover, it serves as a place for opinion and experience pieces regarding tech communities and conferences.
We've found the process of using Git for blog posts helpful. We submit pull requests and receive immediate feedback from our coworkers. Moreover, after officially publishing the article, our readers are allowed to submit pull requests of their own (usually correcting typos, or incorrect code blocks). Furthermore, we can open up GitHub issues to save our blog ideas.
Rob, great post. I especially liked the Ulysses anecdote.
Somewhat irrelevant, but when using Octopress as a blogging platform, do spend some time working on the CSS. Octopress has some great features, however, too many of the generated blogs look similar. By spending a weekend working on it, you can really differentiate your blog and add your own "character" to it.
I haven't spent much time with the CSS, primarily because I wanted to make sure it was going to be worth the effort and that meant getting into the blogging habit. Now that I have a bunch of posts and am starting to get meaningful traffic I'm planning to overhaul the look and also optimize the heck out of it.