WordPress 3.0.1 has been out for a while now, I think the Surfin' Safari blog should be updated to it. I personally have had no issues with WP3 and have found it to be better than WP2.
I didn't realize it is still at version 2.8.5! I strongly urge an update. Using the updater in the dashboard should work fine.
On a side note, I recomend that the admin also install the Health Check plugin as well <http://wordpress.org/extend/plugins/health-check/>, to ensure compatibility with WordPress 3.2 and in future versions it will check for common environment and configuration errors.
WordPress is up to 3.0.5! Someone should really update it. ;)
3.1 has been out for a while now.
WordPress is up-to-date (4.3.1) as of the new site launch.