This was done using OS X 10.6 (Snow Leopard), Windows 7 Professional, and iTunes 10 on both systems. It may work just fine on different versions of the operating systems and iTunes, but I don’t know for certain.
I wanted to move a copy of my rather large iTunes library from the Mac over to the Windows system, which is always on. While it’s easy to setup Home Sharing and then initiate an import of all music over the network, there doesn’t seem to be a way to sync the playlists. I may be mistaken, but I could have sworn that when I first enabled Home Sharing I was able to sync my entire library and playlists from an OS X 10.6 system over to another system running 10.5 (with both running the latest version of iTunes at the time).
Unfortunately, only the files synced with the Windows system. I couldn’t find an easy method for copying playlists that didn’t involve a third-party program.
I decided to take a more direct route and just copy my entire iTunes library manually. To do this I pushed a copy of everything within the iTunes folder to a network drive, deleted everything within the Music\iTunes folder under the Windows account, and then pasted a copy of my library into the Windows iTunes folder.
Note: This will only work if your media is stored within the iTunes folder. If you’ve always had have the option under Advanced to Copy files to iTunes Media Folder when adding to library then you may already be in good shape.
The next time I fired up iTunes in Windows I had my media and the playlists I had setup on the Mac. The only thing I had to change after copying was the name of the iTunes library – it had also copied that from the Mac.
The information and artwork for my movies transferred, but the movie files did not because they were not stored within the iTunes folder. This was expected and preferred – the ASUS hard drive isn’t large enough to also accommodate the movies (I may upgrade the drive in a few months so I can also store the movies there).
I haven’t used the library much but it appears to be working fine.