There has been lots of discussion about how to play random MP3s without playing the iTrip tuning files. Well, I think I’ve got it figured out. If you delete the ID3 tag information from the iTrip mp3s (artist, album, and genre), they won’t show up if you browse by those categories. You can set your iPod to random play however you prefer and those files won’t be in the pool of songs that get randomized.
Play random MP3s on iPod and avoid iTrip files