Q: All of my music videos are imported into iTunes and properly converted to iPod format, but when I go to Preferences and click on the iPod’s “Videos” tab, the “Do not update videos” option is selected and greyed out; I’m unable to select the other options. How am I supposed to synchronize my videos?
A: The video synchronization options are greyed out because you have elected to manually manage your music tracks and playlists.
In this case, you’ll need to manually manage your videos in the same manner as you manually manage your songs: drag and drop.
If you’d like to be able to use one of iTunes’ automatic video synchronization methods, you’ll need to switch from “Manually manage songs and playlists” to one of the two Automatic music synchronization options. These are available in the “Music” tab of the iPod Preference panel in iTunes.