Gabe Weatherhead of Macdrifter had recently moved his site from Wordpress to Pelican, the same engine used to run this site. In this post, he explains how the process he went through with moving data and using RewriteEngine to avoid breaking links. While I chose to adopt the URL scheme of Tumblr and transition to the one that exists today, Gabe chose to use a slightly, yet entirely different URL scheme.
For anybody looking to moving blogging engines or have a need to use RewriteEngine, this is an excellent post to reference.