Today I upgraded a wordpress blog to version 2.5.1 and noticed several plugins are also not up-to-date. The plugin upgrade cannot be any easier, with a single click to upgrade each one. No wget, no FTP, just a click.
Upgrading Drupal modules require a bit more thinking, with various versions available for each modules, plus development snapshots. Lately, the update status module helps simplify the process. But I think the process of actually updating to a chosen version should be reduced to something like the wordpress experience above.