If you are at all interested in sound quality, get the Creative over the iPod any day. I've been using a Creative Jukebox 3 for a little over 2 years now, and I find it indispensable on trips and for moving music from inside to outside, to the car, and from home to office and such. I plug it into some pretty high end systems and it sounds acceptable, considering it's a compressed format. It has line out, so you can use it with the Headroom headphone amps, and digital line out, as well as analog in; you can rip vinyl directly to mp3 if you want to.
The interface is decent enough, and it will automatically make an album into a playlist (with some players the songs play back alphabetically unless you organize them yourself), and there is a really great community that supports the devices, NotMad. NotMad Manager makes your Jukebox appear in windows as a usb drive, allowing drag & drop, windows trees, etc.
Tom
