Just bought a classic and got the check USB memory error after about a week. Storing close to 70GB. Unplugging/plugging back in didnt work. Car on/off didn't work. Finally restoring the iPod did the trick. My iPhone and Touch work fine.
Wonder if it actually does have something to do with how much is on the iPod... Regardless, constantly restoring will get old real fast. I actually stream music over Bluetooth most of the time anyways. Good luck, if all else fails, just restore.
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