Man, I saw the link to the WordPress Automatic Upgrade Plugin, and I thought "Yeah, right, like this is really gonna work". But WP's been bugging me to upgrade from version 2.3.something every time I log in, and it's a Friday night, and I can't be bothered fishing around on the WordPress site to read up on how to do the upgrade, and it's a pain to do the backups, so I went for it.
And you know what? It Just Worked. Migrated all my stuff, kept all my plugins (although, it didn't reactivate them, maybe it wasn't supposed to, I don't remember). Otherwise, it was killer - good feedback, lotsa hand holding and reassurance along the way. Fetched, unpacked and installed the whole thing. Click, click click. And now I have a spiffy new WordPress 2.5.1 install.
Best part? It's free. I made a donation to Keith nonetheless, because he made the upgrade so easy, and to encourage him to keep up the good work. If you've been putting off a WP, hop on over to Keith's site, grab the plugin and try it. I think you'll be happy, and support him, too.