I use iTunes all the time - chances are that your files are simply in the wrong format for the Clip. It is pretty simple to fix. Keep in mind, though, that I use a Mac, so some of these things might not be the same.
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Go to the iTunes Preferences menu (iTunes - Preferences)
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Click the button called “Import Settings . . .”
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Select the import method you prefer (for simplicity sake, you can choose “MP3 Encoder”) from the “Import Using” drop-down menu. You can then choose the setting (quality).
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Once you have done that, go back to your music files in iTunes. Highlight all the songs you want to convert, then either right-click or open up the “Advanced” menu, and choose “Create MP3 version.” Depending on how many files you selected, this may take a while. A new temporary “Converting” playlist will appear in the sidebar, so you can track the progress. Once this is completed, you will then have MP3 versions of your music which you can easily drag and drop into your clip.
The new MP3 files will be in the same folders as the other formats, so make sure you grab the right files to copy to your clip +. One thing to keep in mind is that you can’t create playlists or sync from iTunes - it will only work with iPods.
I hope this helps.
