I don't want to jinx anything, but I think I can tentatively award this round to me. Time will tell to see if everything is working the way I need it to, but so far so good.
When I moved off of Keenspot my long-term plan was to essentially run three sites: Ubersoft.net for the comic, Eviscerati.org for more detailed rants against the excesses of the Computer industry, and Eviscerati.net for... well, I hadn't quite figured that out yet (though I have now). When I originally set everything up I created three different Drupal installations, each with their own modules, their own databases, and their own logins.
This proved to be a royal pain in the neck to keep up to date. When Drupal was updated to 5.2 (a security release, so I needed to update accordingly) I had to upgrade three sites. Whenever a module was updated it had to be added to three sites. You, my readers, would be forced to create three separate accounts -- one for each site -- if you wanted to have editing privileges on the other sites. It was much too difficult to maintain, so I decided to focus on Ubersoft.net and hold off on the other sites until I could solve those problems.