I believe iTunes may not like to sync with not apple players, but I am sure DRM protection is to blame here. You can try to sync your music with the software provided by Zen, or a program called MediaMonkey, to see if it works.
Otherwise, if the music is DRM protected .mp4, you can always burn the songs into a standard AUDIO CD, and then rip the music back to your computer, that way it loses the DRM protection, and should be easy to sync without problems.
http://www.mediamonkey.com
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