After cleaning up "duplicates" in my Library, when I sync any device thereafter some Playlists are missing those songs?

Missing songs from playlists after sync

How did you clean up the duplicates? A playlist is an ordered list of references to tracks in iTunes. If you had duplicates in the library you may have added one version of a track to one playlist and the duplicate to a different list. When you remove the duplicate only the first list contains a reference to the song.
I have a script which would have eliminated duplicates while preserving playlist membership, and merging ratings, play & skip counts etc. More here: Re: When I delete duplicates how do I know which version is the original song and which is the duplicate? If restoring the playlists is important you may be able to restore a previous version of your main iTunes library,itl file that still has the uncorrupted playlists using the techniques in Empty/corrupt iTunes library after upgrade/crash and then run my script to dedupe. If you've updated iTunes regularly however, and don't have some other backup of the .itl, your most recent file is likely to be from last October.
tt2

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