I have debated the same thing for sometime as well. To date I have found that iTunes was the best for me. But not without using the great program form the
Hymn-Project. Simple easy to use program that will convert your iTunes files to .mp3. Then I can do what I want with them, like transfer them to my Axim. Takes a couple of extra steps, but works for me. I like to buy my music rather then rent it al a Yahoo or Napster. But I also like to transfer it to my Axim or Rio. Hymn makes that possible. Good Luck~