Transfering Music from Harddrive to iTunes Library...

Im obviously doing something very wrong. I have all my music on an external hard drive. All I want is to copy them to iTunes library without lots of duplicates. I have changed location in Preferences to search for music on the hard drive (which mysteriously has just changed from E to F?). Each time, I delete the itunes library - then go File - Import Folder to itunes - Select it - then it seems OK. Then I have 11GB worth of duplicates... Last, thing is that it also randomly puts non compilation albums in Compilations. Ive tried moving them, creating folder and moving, but each time I try and get it all sorted, next time I try and copy over successfully again even more albums appear! Sorry for long explanation but would love some help.. Many thanks,

You can't sync or drag your non iTMS music back directly from an iPod to iTunes, the transfer of music is designed by default to be one way from iTunes to iPod. However there is a manual method of accessing the iPod's hard drive and copying songs back to iTunes on Windows posted in this thread: MacMuse - iPod to iTunes
If you prefer something more automated then there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod, this is just a selection. Have a look at the web pages and documentation for these, they are generally quite straightforward. As iTunes 7 is just out some of these may not work with it yet though I haven't experienced any problems with the Mac software I use.
YamiPod Mac and Windows Versions
iGadget Windows Only
iPodCopy Mac and Windows Versions
iPod Access Mac and Windows Versions
PodUtil Mac and Windows Versions
iPodCopy Mac and Windows Versions
PodPlayer Windows Only
There is a new function in iTunes 7 under File, "Transfer Purchases from iPod" which transfers iTMS purchases that you can check out. A paragraph on it has been added to this article: How to use your iPod to move your music to a new computer

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