IPod will not play songs bought from iTunes more than once

None of the songs I have purchased from the iTunes Store play on my iPod. They play on my Mac, my wife's Mac and my wife's iShuffle, but not my iPod. My iPod is running the lastest software version, and i have the latest iTunes version.
If I format, reset, restore and reload my music, HOORAH!! they play...ONCE. Then I have to do that all over again if I want to play them again. The songs say they are there, they say they are taking up hdd space, but if I try to play the iPod just thinks about it for a second or two and then skips over the song.
I have never had any problem with songs ripped off my CD collection.
Apple are completely useless and offer no assistance and what i have been able to find on their website tells me to do what I've done. Does anyone have any ideas how to make my iPod compatible with the iTunes store?

This just happened to me on one song I purchased from iTunes (it plays fine on iTunes on my MacBook). I'm on iTunes 8.0 (haven't yet upgraded to newest version). Everything else works fine so should I do this for only one song - or is there another easier fix? I did copy the song to a cd so would it work if I just deleted the one song and imported it? Or is this a sign of a deeper problem?

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