Song shows up in playlist on iTunes, but not on the iPod Touch

So I bought a song from iTunes on my iPod Touch, and so it shows up on the "Purchased" playlist, and I can listen to it. So, I sync up to my PC (or my wife's MacBook Pro, doesn't matter) and using iTunes, I add the song to a playlist of my current favorites. I then sync the iPod. In iTunes, it shows the song as part of the playlist, and shows that there are 24 songs in it. But when I unhook the iPod and look at that exact same playlist, the new song does not show up, and it says that there are 23 songs in the playlist.
I have already tried deleting the playlist, creating a whole new one, and I can put any song I want in there, except for this one. ??? Anyone heard of this before?

If the song is in iTunes, and it is in a playlist that you auto-sync your Touch to, then the only things that might cause this problem are:
1- Is this new song un-checked in iTunes? If your Touch is set to sync only checked items that would prevent it from syncing. If that's the case, just enable the checkmark next to the new song and re-sync.
2- Is this playlist a smart playlist that is forced to be limited in size? If so, there is a bug with the 3.1.x OS such that smart playlists that are limited in size will have different contents (and sorted differently) when you compare the playlist on iTunes vs. on the Touch. The solution in this case is to disable Live Updating in the smart playlist definition, then the two versions of the playlist will agree.
3- Is the new song tagged as "Skip when Shuffling"? If so, and if your Touch is in shuffle mode, then the song count in the playlist will not include songs that are designated to be skipped.
See if any of those three things are what is going on. If not, then perhaps you need to reset or restore your Touch, but I doubt that.

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