Finally made some progress on the CMS. It turns out that firing up LWP and automating the building of most of the database from the existing site does a good job of removing scary barriers.
The new site (I've restructured and changed the design while maintaining the same URLs (Good URLs don't change)) is up for testing at http://stone.thecoreworlds.net/ (for the time being).
Internet Explorer has bugs (oh big surprise there) which I'll try to hammer out before pushing it onto my main site. I've also got to rewrite a good chunk of the About section (since some of it is out of date, reflects opinions I no longer hold, or simply isn't written well) and add blurb to each category index page. That last bit will be easier once I add a front end to the edit page for Category objects.