Alright, screw it.
I've got to get moving in a direction so I'm going to swap this server over to WP tonight. Yes, tonight. After three years of using my own custom code, I'm moving on to someone else's blogging platform. I wrote down all the things I had to finish up on my custom server and then wrote down the steps I needed to do move to WP (and the things I would miss - like my favorites) and decided to go with WP.
Steps (and difficulty):
1) Install WP code and install new DB (easy)
2) Import existing weblog and comments into WP (relatively easy)
3) Move media files over (relatively easy)
4) Fix URLs with mod_rewrite .htaccess (medium)
5) Convert web design template (medium)
6) Add Favorites page to import from Bloglines (hard)
Okay. Let's get started - I'll try to make sure any comments left after this post get moved over. My apologies in advance for the RSS refresh.
Update: Import is done, swap has been swapped. Now working on the template...
Update 2: The template is going to take a while because I'm going to mess with it a ton. Probably a good time to update my 5 year old photo as well with one that looks like me now.