Apple / iTunes and even iPhoto are very controlling in their programs. It's too complicated in my mind to get your files out of their programs (often requiring going through the file system to find the root file or having go through an 'export' process first).

Also, try copying the same music from your itunes to multiple devices and back again. Oh DRM.. how much we hate thee.

Removing your files from these programs (while great programs) is often difficult. Even as a mac fanboy myself, it frustrates me about apple's programs.