My father-in-law, Fred, recently wrote an email to the family requesting advice on MP3 players. He wants to buy one, and he's going to both buy music on line and rip his own CDs. You should also be aware that, while Fred is a long-time computer user, he's no techie or gadget guy.
I recommended the Apple solution to him, the iPod and iTunes, because it is brain-dead simple to use the complete solution. The software is easy to use, the store is cleanly integrated with the software, and the click-wheel controls and menus are all absolutely intuitive. In addition, the accessory offerings, like external speakers and carrying cases, are much broader because of iPod's market leadership position.
My sister-in-law, Laura, enjoys her Creative Zen Micro, which she uses to listen to her own ripped song collection.
Coincidentally, the NY Times published a review of the non-Nano MP3 players. While the title, "Singing the Praises of the Non-Nano," would indicate that they had raves for the other players, I certainly didn't get that feeling, particularly when you consider the complete offering.
The bottom line for me is that I have tremendous appreciation for Apple's design abilities, and even though I also sometimes bristle at their "sledgehammer marketing" (including their digital rights management stance), I will continue to lust after and buy their products.
And, I will enjoy seeing the failure of Microsoft's new Zune player, as I enjoyed seeing the failure of Dell's.