In keeping with an apparent tradition, I will discuss the process of moving my data from Wordpress.com to Octopress. It was not an entirely trouble-free process. All of the following advice applies to Jekyll, not just Octopress.
First of all, the default migration script failed to run. I couldn't find any advice on the subject online, so I decided to try exitwp instead.
Once you have cloned the repo you need to install the dependencies. The instructions on Github are linux-specific. The only tricky part is that you need to install libyaml. Instead of using apt-get, just grab it from homebrew:
brew install libyaml
Then you can run:
pip install --upgrade -r pip_requirements.txt
This step will compile libyaml. Note that if you are not using virtualenv (see below) you should preface that command with
Mac OS X Lion does not come with pip installed. You can follow the instructions here: http://www.pip-installer.org/en/latest/installing.html
Note that the recommended way to get pip is via virtualenv. Virtualenv is essentially the Python equivalent of RVM (discussed often on this blog). However to achieve feature-parity with RVM you also need virtualenvwrapper.
If you have not set up Python on your Mac with virtualenv/virtualenvwrapper I highly recommend you do so. I have written a walkthrough that updates the information available at the links already mentioned.
Once you have gotten exitwp and its dependencies installed, simply drag the xml file you exported from wordpress (under Dashboard > Tools > Export) into the exitwp/wordpress-xml folder. Then run:
If you're lucky, that's all there is to it. Your posts will be converted to markdown and saved to the exitwp/build/jekyll/username.wordpress.com/_posts folder. But I got an error message from the XML parser.
Apparently this is common as Wordpress doesn't do the greatest job of formatting the XML. This wasn't a big deal, though. I just ran it through xmllint (which should be preinstalled in OS X) and fixed the two or three errors by hand. If you have TextMate handy, just open it in there and run Bundles > XML > Validate Syntax.