I just upgraded (manually) this site to test out the new 2.5 version of WordPress. I’m totally in love with the new interface! (Here’s more detailed account of all the great new features in 2.5 here) It’s elegant and such an upgrade for usability.
Anyway, one of the new features with 2.5 is it includes links to the plugin repository in the Dashboard and I just found a great plugin called WordPress Automatic Upgrade.
It automates the upgrading process …. and I tried it out on a 2.3.3 version blog and it worked great. All I did was upload the plugin, activate it and start the process.
Upgrading can be scary the first time you do it (not with the plugin) … but if you’re really scared, go ahead and manually export and backup your blog before doing so (even though this plugin does it for you).