Sync Manager Help and Playlist H

I have almost 3,000 .mp3's, but when I use Sync manager, it only finds about 500 of them for my Zen Vision:M. All my songs are in my iTunes folder, but that shouldn't matter. Any ideas?
Actually, I found a way to make playlists on my Zen by dragging files from my iTunes playlist into the playlist creator in Media Explorer. Problem is, if I want to make multiple playlists in this manner with some overlap of songs, Media Explorer loads the overlapped songs twice on my Zen, which is no good. Is there any way to avoid this?
Sigh, I should have bought an iPod... or at least a Mac, so I could sync my Zen with iTunes. I wish someone would write a program for Zen/Windows/iTunes sync.
This is what I get for going against the grain - inconvenience. :/

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