For Zip! to iPod: Zipped iofy content will not show up in your iTunes library. Although the files zip through iTunes, on their way to your iPod, they are not added to your computer's hard drive.
For Zip! to Windows Media Player: Zipped iofy content will appear in your Media Player library. These files will stay in your library as "Secure WMA" files, and can be played from within Windows Media Player (as well as on your PlaysForSure device).