Today I successfully upgraded my Wordpress installation from 2.6.something to 2.8.4. The upgrade went very smoothly by following the directions in the Wordpress Codex. There are a few reasons why I decided to take the plunge and go ahead:

• WP_DBManager is a nice plug-in that will perform periodic backups of your database. This plugin requires Wordpress 2.8 or higher.
• But more importantly I really like the new dashboard layout. Everything is there and easy to find. The quick-edit feature for posts and pages is a real time saver. And so far all my plugins are still working!

Make sure you remember to save wp-config.php from your old version of Wordpress. This contains the database access info and must be copied into the new installation.