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Not sure that itunes accepts all different movie formats, I tried it a while back and I think it only allows .mov files? Correct me if I am wrong..

What version of windows are you running? Most vista installs these days come with Media Centre installed, you could possibly use that as a library if you have it. Or you could possibly buy something like this - http://www.bolidesoft.com/allmymovies.html Ive never used it, but seems to be...