How to find corrupted music files causing sync problems (dotted grey circle)?

I'm having the dreaded dotted grey circle problem and it's driving me mad.  Based on what I read in the for a it could be because a new music upload is corrupted, but how do I find it, when each try to sync last two hours?  And then to de-sync again lasts another half hour, to resync again lasts another two hours ... My life is not long enough for this crap!
Often I have no idea what it's doing - "waiting for changes ..." ... should I wait hours for something happen only to realise nothing's happening??

Is that even possible? We're talking about a 6-year-old iPod thereabouts.

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    Message Edited by lameplanet on 06-May-2009 06:11 PM
    Message Edited by lameplanet on 06-May-2009 06:12 PM

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