Manual Update: Update Playlist?

In iTunes, if I drag a recently updated Playlist to my iPod, I get dupes in the Pod's Library of the tunes that previously lived in the Playlist.
I have a 2G Pod that can't hold all of my Library, so it's set to manual update. After adding a few tunes to a particular playlist in iTunes, if I drag the playlist to the Pod to update the playlist, I get duplicate tunes in my Pod's Library. Two each for every old tune in the Playlist.
I've tried first deleting the Pod playlist before updating, which worked exactly once, but every time since trying this method, it results in dupes. I wish Option-Delete worked for iPod Playlists.
Is this normal behavior, or is there a pref I can kill that might fix this? As you know, hunting down dupes on a Pod is a pain, and an Applescript isn't that helpful here.
Worst case I suppose I could enable Playlist Sync for the Pod, but I'd be relegated to Checkbox ****; I have well over a 100 Playlists. I'm not in a hurry to go down this road.
Dual 2 Ghz G5   Mac OS X (10.4.6)   Nano, 2G iPod, video iPod

Didn't you just answer your own question. If you are already updating to a playlist then update the playlist then hook the pod up to sync.

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