...a lot of people are missing the point surrounding iTunes. Whether you can choose to use it or not, Apple allow you to go to their website and download it for zero benk, and then use it to organise your media collection.
So, let's say you do this. You don't have a portable player, but have a massive cd collection that you've ripped, or mp3s that you've download from legal/illegal sources. You download iTunes, organise your media collection, grab some album artwork, maybe buy some new DRM free stuff from the Music Store.
Then you think to yourself "wow, my music collection is truly organised now. I'd really like to get a portable player so I can listen to this stuff on the go."
After you've spent all those hours doing the work, your only choice is Apple. Yes, you can buy something else, but you're then going to have to spend hours reorganising, and if you want to buy from iTunes, you have to keep 2 software libraries in sync. Joe Public just isn't going to do it.
And to be frank, why should they? Yes, Palm have probably gone about this completely the wrong way, but if Apple are selling DRM free music, and offering iTunes for nish on their website, they should at least allow other companies to fully sync with it. Not just playlist sync, but full syncing. They shouldn't necessarily have to provide end user support, but they shouldn't be bloody well allowed to offer a free piece of software to rope you in, and then only leave you with one choice of hardware.