Its something of a bodge job, but why not make a playlist of your entire library?
You don't need to make a playlist of your library to shuffle it on the iPod. Like I said, the iPod will remember where it left off, assuming you didn't somehow cut it out of shuffle. It won't solve the problem in iTunes either, because iTunes doesn't remember where it left off. Making a playlist of your entire library would be pointless in this regard.
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Cheers! :-) - JediJoker
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