IPod skips and pauses after update

After updating to the most recent software my iPod Photo (20GB) started acting up.
* I can't automatically update my playlists (Error Message: "This iPod can not be copied to" appears after about a third of the songs have been successfully updated). I can then manually copy the rest of them one by one. Tedious!
* iPod skips and freezes on certain songs
* Resetting, restoring, re-installing software (iPod and iTunes) does not take care of the problem
* Songs play beautifully in iTunes and on my other iPod (nano)
Please help.
G5   Mac OS X (10.4.3)  

I'm afraid I won't be any help to you, but I DO HOPE someone can enlighten us. I am also having this problem and I have just now exchanged my Nano for the second time because of this loose connection. I suspected the earphones immediately. If I lay the iPod on a flat surface 2 feet behind me without arm/hand interferance and sit like a statue without blinking or breaking a smile, I'm good. But once I breath the earphones disconnect. Would I be soo dumb to think it was because I got the Nano Silver instead of the Green? One friend has a Green and the other has Red. They both have "snap in" solid connections. I'm on my third set of earphones and second car transmitter. NOT making any difference. Someone please....do I keep exchanging this thing until I find a "snappy" earphone hole?

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