ITunes and iPod show different number of songs for same playlist

Alright Apple.
I have been having this problem EVERY time I add new songs to my playlist. My songs sync up, as it shows up in my entire music library, but the playlist is missing songs all of a sudden. Somehow I am able to get out of it sometimes, but I don't know how. I've Googled every thing and I have tried every "IT support" trick in the book including rebooting the ipod and my computer, unplugging and replugging, resyncing, unsyncing and resyncing, and making sure the song is checked, and making sure that music is set to sync in the iPod settings in iTunes. Here's what it looks like:
I have 367 songs in this playlist, but on the iPod, it only shows 360. I can't get it out of this state right now.
I have an iPod Touch 4th Generation with iOS 5.1.1.
The PC I'm syncing with is Windows 7 with SP1
iTunes 10.6.1.7.
It's an ASUS UL30Vt
I also have an iPod Touch 2nd Generation that I was planning to sell, but it doesn't have this problem.

How many music videos do you have? When I first got my iPod I had this same problem and it turned out that the music videos showed up under the music tab. When I'd check the music count on my iPod it was less by exactly the number of music videos I had. The music videos on the iPod were in the Video section.

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