Unable to drag and drop playlist to iPod

I have a 30 GB iPod Classic which I manage via iTunes on Windows 7. I manually manage which songs, playlists, etc, are synced to the iPod, since my music collection is somewhat bigger than 30 GB.
I recently made a new playlist on iTunes with a lot of songs (about 2,700) and attempted to drag and drop the playlist onto my iPod. Sadly, iTunes won't allow me to do so, and does not offer any diagnostic or error messages to tell me what the problem is. Just the preceding day I was able to drag-and-drop a playlist with about half as many songs onto the iPod. All or almost all of the songs on the new playlist are already on the iPod, and there is 3 GB of space free on the iPod.
Any idea what the problem is? Is there a limit to max playlist size?
Thanks in advance,
-PT

OK, it's actually a latency problem: when you drag and drop a REALLY LONG playlist to an iPod, it doesn't immediately figure out what you are trying to do (or else it's polling the music list on the iPod and comparing it to the playlist, I don't know). So you have to drag the playlist and hold it over the iPod icon in iTunes until the iPod icon opens up, then drop it.

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