I have seen this several times when creating a MP3 DIRECT from I-tunes. The way to solve it and you can test it with your top 10 songs is to create a playlist of the songs, burn this playlist to a CD. Then import the songs from the CD and set preferences to create a MP3 when importing.
Then copy this MP3 file on to your USB and you are good to go.
Enjoy the Ride!
2013 RGU in Big Blue Pearl
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S&S Power Tune Duals w/V&H Slash Cuts, TTS Mastertune, Daymaker Headlights, Hawg Wired RS 400 amps, J&M Rokker speakers, AN Big Sucker, Corbin Dual Touring Saddle, Madstad, Progressive Monotubes, JRI Shocks, All LED lights, & several Chrome Goodies.