There are a lot of nice things about the iTunes (and Apple in general) ecosystem. As long as the way you want to work is the same as the way Apple built it, things are generally hunky-dory, easy to use, and reliable. Stray away from Apple orthodoxy, though, and things can get ugly really fast. A prime example of this is trying to keep one iPod/iPad/iPhone in sync with an iTunes library through multiple computers.
Between Apple and the recording industry's piracy paranoia, they have contrived to make it very difficult to plug a device into multiple
