Songs you've purchased legally, such as through Apple's iTunes store, often come embedded with DRM (digital rights management) encoding. This ensures that you can't illegally copy those songs onto other devices, protecting the rights of the musicians and publishers of those songs. There are ways to legally copy songs from one iPod to another---under certain circumstances.
Transferring Your Files
If your Mac has died and you've got your songs on your iPod, you can purchase software called Podworks that legally allows you to transfer songs from your iPod onto your new Mac. From there, you can transfer those songs to another iPod as well, if you wish. This software does not alter or harm the DRM encoding in any way. Unfortunately, as of September 2009, there's no PC version of this software. You may want to back your songs up onto multiple iPods in case an irreparable crash ever does happen to your PC.
Sharing Your Files
Some songs are perfectly legal to share, such as downloads that artists have made available for free. As of September 2009, Apple has now made non-DRM-encoded versions of songs available for sale via the iTunes store as well. If you and your twin sister both want to share an album that you've split the download fees for, you can---legally. Download the songs onto your computer via iTunes, and then transfer them to each iPod. If you make this kind of downloading a habit, you can quite legally and easily transfer songs between iPods---provided you hook them up to your computer first.
The good news with this approach is that it will work for both PCs and Macs. Make sure you purchase non-DRM-encoded songs and you'll have no problems---hardware, legal, or otherwise. The iTunes program will walk you through the process of transferring songs from your iPod to your computer, as well as from your computer to your iPod. Chances are excellent that if you've already got songs on your iPod, you're familiar with this process. The key to your success is simply paying a little more to buy non-DRM songs
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