Copy Songs from iPod to Zune

Bebe asks, “Is it possible to transfer music from an iPod to a Zune?”
There’s no direct way to copy files from an iPod to a Zune. Files purchased from iTunes music store will not play on a Zune, just as files purchased from Zune Marketplace won’t play on an iPod. There are some tools you can use to get songs from your iPod to your Zune and get them all to play, but you have to be prepared to spend a little money or a whole bunch of time.

Copying Songs Purchased from iTunes Music Store
If you purchased songs from the iTunes Music Store, there are two ways to get the tracks your Zune. The easiest way to make them available to your Zune is to download SoundTaxi and let it convert all the files to a format you can play on the Zune. Option two is to burn the songs onto an audio CD using iTunes and then ripping the CD using the Zune software. I walk through the process of copying iTunes music to a PSP, which is almost the same for Zune.
I’m personally not inclined to hassle with all the re-ripping of tracks and will simply pay a monthly fee for the Zune subscription service once my MTV URGE service expires next year. That gives me millions of songs to listen to and when the next great new device comes out, I’ll simply stop paying for Zune music and get all the same tracks on whatever the next new thing happens to be.
Zune Software and iTunes
If you have MP3 files in iTunes that are also on your iPod, you can get these files on a Zune with relative ease. By default, Zune automatically watches the My Music folder in your My Documents folder. iTunes typically creates a subfolder for your iTunes music library in this folder, which also automatically gets added to the Zune library. Assuming you have any MP3 files in the iTunes music library, the files will be available in the Zune software.
Copying Songs from an iPod
If the songs you want to copy are on an iPod, but not on the computer you installed the Zune software on, you need to use different software to get the songs off the iPod onto the Zune. My favorite software for backing up an iPod to a computer is iPod Access. It’s not free, but it does have a fully functional 14-day free trial. Copy the songs from your iPod to your computer hard drive with iPod Access. Add the folder with the songs from your iPod to the watched folders in Zune by clicking the Options button and choosing Library > More Options from the menu. Click the Monitor Folders button and add the iPod Access folder to the list of watched folders. This process will put all MP3 files on your iPod into the Zune library.