Synching iPod with playlists

I have a playlist with duplicate songs listed. I purposely did it this way. When I sync with my iPod it just creates one instance of the song. How can I get it so that all instances of songs get synched.
Thanks.

Playlists don't contain any songs at all. They are simply pointers to the song file.
You don't need the song on the iPod twice. If you have it twice in a playlist and play that list, it will play the song twice.
If you make one playlist with the same song 100 times and sync only that playlist, you will only have that song 1 time on the iPod.

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