Music plays in iTunes, but not on iPod

Bought an iPod Classic 120GB recently.  Roughly half of my music will play on the iPod, but all of it plays on my PC.  I have resynced multiple times and actually traded it in through the Apple store thinking that might be a quick fix.  Still the problem persists.  For example, some songs on an album will play, while others will be skipped.  All are encoded the same way, V0.  When I convert into another bitrate, the problem goes away, but I'm not going to be doing that to my entire music library.  The iPod classic does advertise being able to play variable bitrate encoding, so I'm wondering if there is any fix for this problem.

Usually unchecking the song(s) in iTUnes, updating the ipod, then checking the songs and updating the ipod again will fix the problem.
If not restoring it with the latest ipod updater (06-28-2006) should fix it. Restoring wipes the ipod clean and then you use iTUnes to load it back up with your music

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