itunes presents several problems for an advanced user to work around. If you have multiple computers, keeping the libraries in the different computers synchronized is a difficult and non-trivial task even for an advanced user.
I finally copied all my music into the new vista PC with a 300G hard drive. However, due to the paranoia about losing any content, i ended up with multiple copies of my music files in different harddrives and computers. Beyond Compare and Check Identical Files are the 2 software that i used to minimize file duplication. But a strange thing happens when you move files and then get itunes to rescan the folders. itunes creates duplicate copies of files itself (and i have not kept track of the exact conditions that trigger this). For example, in your itunes folder: c:\users\joe\itunesmusic\myalbum\song.mp3 existed before itunes would create: c:\users\joe\itunesmusic\myalbum\song 1.mp3
This effectively duplicated my entire collection. i had to create a perl script to clean this mess (see my other post today on this)
I then used: ITLU (itunes library updater) utility to cleanup itunes database. After removing the files, running itlu can scan and identify orphan entries and it will clean them up.
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