Originally Posted by Puppetman
And the solution is to reboot.
I believe that my iPod Touch being plugged in caused the problem. I am going to play around as time permits and come up with a set of steps to recreate, and maybe the bug can be fixed.
If you go to Preferences - Plugins - Device Interface plugins you can disable the Apple plugin. This will prevent the iPod from interfering in the future but still allow you to use the Connect to iTunes feature.