Drupal updates are tedious--downloading individual files, uploading, manually running the update.php script... If you're administering more than one Drupal installation, it becomes tiring quickly. I've found two ways of solving these problems: the Drush utility and using Acquia's Drupal distribution.

Drush

Drush (http://drupal.org/project/drush), the "Drupal Shell" is a php script that automates updates, installation and removal of Drupal modules through the command line. Updating your Drupal modules is as easy as entering drush update in your SSH session. Likewise, "enable" "disable" and "uninstall" handle common module operations.

The biggest weakness with Drush is that it is currently unable to update Drupal itself. To apply a security update will require more command-line interaction. This is the method I use:

$ wget {path to drupal upgrade online, ex:http://ftp.drupal.org/files/projects/drupal-6.13.tar.gz}

$ tar -xvzf {path to file, in this case ./drupal-6.13.tar.gz}

$ rm -rf ./drupal-6.13/sites

$ cp -rf ./drupal-6.13/* ./

Of course, all of this should take place in the root of your drupal installation. We remove the sites directory prior to overwriting the existing Drupal files to preserve customization in the existing sites folder.

Pretty simple!

Acquia Drupal

If you are intimidated by the command line, or don't have SSH access to your webhost, Acquia Drupal might be more your speed. Acquia is a customized distribution of Drupal, targeted toward providing an easy to use Drupal for building online communities. (Find more information here: http://acquia.com/)

Acquia essentially integrates a few commonly used Drupal modules into their system, and provides a method for updating Drupal/modules through their own SVN repository. This is best demonstrated by this screencast: http://acquia.com/community/resources/acquia-tv/updating-acquia-drupal-svn-repository

If you are planning on building a site using primarily the modules in the Acquia distribution, then this would be a good choice-- a couple commands updates the whole shebang. On the other hand, if you are going to use modules that are outside of Acquia, you will have to manually update them... saving you very little time. Also, ideally you'd choose to use Acquia before building your site. If you have an existing site, it CAN be ported to Acquia, but the additional work required probably negates the convenience of the updates (IMHO).

In any case, I have used Drush for awhile now and been a happy customer. I recommend it for anyone with basic familiarity with the command-line.