IPod touch no longer synching playlists

Hi,
A couple of days ago, my iPod Touch no longer syncs playlists. I have a couple of playlists with a few hundred songs. The playlist shows up on the iPod in the playlist menu, but if you go into the playlist, it only shows 2 or 3 songs. But if you go under songs, all the songs are there.
Steps I've taken to fix this:
1. Reset iPod. No change.
2. Deleted and created a bunch of entirely new playlists, error still occurs.
3. Restored iPod to factory settings. No change.
4. Uninstalled iTunes and reinstalled. No change.
Has anyone seen this before? It's very annoying. I'm stuck listening to all my songs on shuffle, even if I just wanted to listen to a select few I put in the playlist.

Auto-synching.
The playlist is a Smart Playlist, created with the following rule:
"name" "starts with" and then the letter, which I change daily.
Options checked are:
Limit to 10gb selected by random
Match Only Checked Items
Live Updating
Again, when I sync, all the songs make it over, but the playlist is empty or only contains a couple of songs. This only seems to happen with Smart Playlists. If I select all the songs in the smart playlist, then create a new playlist based on the selection, this will sync properly.

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