WordPress 2.3 introduced the Upgrade Automatically Feature for plugins. In the plugin list there is a notification for plugins that have updates and they are easily updated by supplying ftp login information.
This was a great addition to WordPress. No longer did I have to check and see if a plugin had been updated, download it, extract the zip file and upload the files to my webhost. It was such a tedious process that my plugins did not get updated very often. Now, I can just click “Upgrade Automatically”, type in my login, and the plugin gets updated. Yesterday there was a problem auto upgrading Google Sitemaps but it was easy enough to correct manually and this is the only problem I have had with this feature.