You have to be careful, as iTunes is a database and runs on links to files.
This means sometimes you can have duplicate entries in itunes to the same file, or, duplicate entries and files.
This is generally an issue if your reencode stuff.
One really good thing I have been doing for some time, is creating a playlist of unrated songs (smart playlist), and listening to it to rate the songs (using the star system).
There is also another awesome field now in itunes which indicates when the song was last skipped. You add this variable to your playlist and then exclude all those that have been skipped in the past eg. 3 months.
Hope this helps,
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