Ok, so I’m almost a year behind, but I finally upgraded from WordPress 2.x to 3.x (3.1 as of today). I quickly made a database backup and used the “upgrade automatically” button inside the Dashboard. I’ve been running the automatic version updates without any problems so I expected the version upgrade to work just as seamlessly. Even the manual installation and upgrades worked well, but those are even simpler now. Thanks, WordPress, for improving the process so much over the years.