Check Version Tracker for apps that can do what you are asking. There are a lot of them out there, just search for iPod on Version Tracker and you'll find something. Good luck.
I did see one case were someone's playlist got a bit messed up somehow. It got converted to mac-ascii somehow (when it declares itself to be UTF), opening it in BBEdit, switching the encoding, and re-saving did the trick to solve it.
PS... to figure this out i simply launched iTunes from the command line, and it basically told me what the problem was...
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PS... to figure this out i simply launched iTunes from the command line, and it basically told me what the problem was...