Some playlists won't sync, why and how to fix?

So far I have found 5 playlists on my iTunes library that won't sync to my iPod. I have no issue with my previous iPod or my iPhone with those playlists but only with my late 2009 issue iPod classic (160GB).
Anyone know why or how to correct this issue?

More Information:
The the difference in the Smart Playlists that appear in the iTunes left-side folder panel but not in the Devices/iPod/Music tab panel and those that appear in both is that they all contain the Match All rule term: "Playlist is ".
I need that rule because I load only a subset (about 9,000 songs) of the songs on iTunes onto my iPod Classic. I use a Non-Smart Playlist ("My iPod List") to enumerate those songs. Thus the various Smart Playlists need to be conditioned on that ("My iPod List") Playlist subset so that they do not load other songs from iTunes. This used to work just fine. One of the upgrade revisions to iTunes (9?) or the iPod broke it. Smart Playlist Rules that reference other Smart Playlist still work correctly.
Can this bug be fixed?

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Some playlists won't sync, why and how to fix?

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