I've never bought an iTune and I don't own an iPod. I think Apple's DRM is awful and represents a major step back for us all. I think those that are investing in iTune digital libraries are suckers. You are basically betting that Apple's proprietary DRM laced format will be the standard for the rest of your life. You are paying too much for your music and tying yourself to only Apple products going forward. More innovative ways to play your music may indeed come in the future but unless they are marketed by Apple you will not likely be able to use these devices with your iTunes files due to Apple's tight proprietary control.
Personally I want nothing to do with it. I still collect my digital music the old fashioned way, I rip it straight from CDs to crystal clear high bit rate DRM free mp3s. These files of course can be played on any device and represent better value in my opinion for today's consumer.
What happens when the killer phone is finally here? You know the one, built in terabyte of storage, lightening fast file transfer speeds, full satellite radio, a breathalyzer, your car and house key, a tiny little thing the size of credit card with a 12 mega pixel camera on it (hey it's the future right, we can dream).
What happens when this phone is out and you really want it and unfortunately Apple didn't make it? That's right, you're a sucker then aren't you. I thought so. You paid all that good money for your iTunes and now you can't put them on your new phone because your new phone threatens Apple's dominance. So who owns the music anyway? You or them? They do. You bought nothing. You bought the right to play their song on their product. It might work today. But I'm not about to bet that this will be the format du jour 10 years from now.