How to transfer Itunes library from Windows XP to new Imac?

Question

I have just purchased a new Imac and want to transfer my Itunes library from my Windows XP pc to new Imac. I have both computers on an Airport wireless home network. If this proves to be difficult, can I use a jump drive? Thanks
iMac   Mac OS X (10.4.5)  

Answer 1

I just got a shiny new Mac, and don't want to lose my music library!
No need! iTunes for Windows is almost exactly identical to iTunes for Mac, and switching over is actually very easy.
First thing you're going to have to do is figure out a data route. Although you can technically use CDs or DVDs, in order to best transfer all data, including playlists and ratings, you'll want another method.
If you have a network set up, you're good to go.
An external hard drive will work as well, just remember that Windows won't read a Mac formatted disk. The iPod is also an external hard drive, and can be used in the same way.
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Once you have the method set up, you're going to have to prepare iTunes.
Open iTunes for Windows, and hit Edit>Preferences>Advanced, and make sure that the folder listed is \My Documents\My Music\iTunes\iTunes Music.
Next, hit Consolidate Music Library. This action is irreversible, and it will make sure that all of your music is put in the aforementioned 'iTunes Music' folder. Shut iTunes, and move on.
Now you're going to have to move the info to the Mac. If you have an external hard drive, drag the iTunes folder, located within My Documents\My Music onto it. If you have a network set up, copy the iTunes folder to a location that can be accessed by the Mac.
Now, on the Mac, open either the external HDD, or the network folder, and copy the folder iTunes to the Home/Music folder.
Start up iTunes on the Mac, and everything should be in place.
Cleaning up
If you have music purchased from the iTunes Music Store, you're going to have to authorize your Mac. If you're not going to be using your Windows machine for iTMS songs anymore, you may want to deauthorize it. Either way, this article has all of the information you need: http://docs.info.apple.com/article.html?artnum=93014
If you're not going to be using the Windows machine for music, you can safely delete the music from it, as it is now on the Mac. However, unless it is actually bothering you there, there's no reason to do so. Redundancy is great for data.
About an iPod:
First, Apple has a doc about using the iPod to switch. It has some great info about moving your documents, emails, etc. However, the method of music transfer there doesn't save most of your library data.
Second, you may want to reformat your iPod for the Mac. The advantage, basically, is some transfer speed. The disadvantage is Windows' inability to read Mac disks without 3rd party software. Either way, the doc on formatting (restoring) is here: http://docs.info.apple.com/article.html?artnum=60983#One
That's it! Your music collection should be up and running in iTunes for Mac. A couple of places to check out, both showing the 'extras' of the Mac version of iTunes vs. Windows:
Doug's AppleScripts for iTunes
VersionTracker
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With a lot of help from DC