Switching from a Mac to a PC, I needed to move my iTunes library from my old Mac to my new PC, without losing any of my playlists, ratings, etc. From my inital Google searches, it looked hard. Moving my iTunes library from my Mac to my PC didn’t turn out to be bad at all, modulo my initial long walks down wrong paths.
It’s not possible to just move your music files from your Mac to your PC; iTunes won’t know where they are. The good part is, iTunes seems to use more than just an absolute path to the music file to identify said file for your library; this makes the job a *lot* easier. The problem is, whatever iTunes seems to use besides the path only seems to work when you’ve let iTunes organize your library for you.
The first step is, therefore, to let iTunes organize your music for you. There’s no particular reason not to do that, although lots of people don’t; I don’t remember the last time I used the file browser, rather than iTunes’s interface, and I bet you don’t either. Go to iTunes>Preferences, click on the Advanced tab, choose a music location you’re comfortable with, check next to “Keep iTunes Music Folder organized”. Then go to Advanced>Consolidate Library. iTunes will take quite a while to put all of your music in one single, well-organized folder.
The next step is to install iTunes on your PC. After installing, run it once. This will put all of the folders and files in their default locations, which will come in handy when you replace them. Quit iTunes before moving to the next step.
Now copy your iTunes Music folder from your Mac to your PC, placing your music in your default “iTunes Music” folder in your “iTunes” folder in your “My Music” folder that iTunes created for you the first time you ran it. Also copy your “iTunes 4 Music Library” file.
iTunes will also have created “iTunes 4 Music Library.itl” and “iTunes Music Library.xml”. It’s not clear what the .xml file does. Ignore it. Delete “iTunes 4 Music Library.itl” and replace it with your “iTunes 4 Music Library” from your Mac, adding the “.itl” extension by hand. Now launch iTunes again. Presto! You’ve moved your iTunes library from your Mac to your PC.