With iTunes 7, Apple has given users the ability to sync the songs in their “Purchased” category between multiple machines. The biggest complaint about this feature is that it only lets you transfer songs that are from the iTunes Store, however much like the “Analog Hole” Apple has also given us a work around.
If you're the kind of person that likes having a playlist of all your purchased music, the default purchases playlist will no longer fit your needs. So before we get going, you may want to make a smart playlist with “Kind Contains Protected” as the rule. This playlist is handy to have even if you don't use it on a daily basis, so I highly suggest you make one eventually. Now that you've done that, just follow these instructions:
Step 1: Select all files in the category you choose (Music, TV Shows, Movies, Podcasts, or Audiobooks are compatible with this method).
Step 2: Drag and drop those files onto the “Purchased” category.
Step 3: To keep it up to date just periodically drag your “Recently Added” playlist to “Purchased” or do so manually. Keeping up with your music is the most tedious part of this method.
Once you do this you will be able to transfer your media to multiple machines. This will work with Automatic or Manual Syncing. If you would like your iPod to transfer files between PC and MAC iTunes, you are going to have to format your iPod with Windows, and then do this method. A Windows formated iPod will sync with a Mac for it's main machine. The only drawback with this is that Windows formatted iPod are in FAT32, meaning the name of the iPod will show up as all capital letters in OS X even after renaming it.
