I just bought my first apple product: the iPod Shuffle (I got the 1gb version)
In short: it absolutely rocks. Software installed perfectly on my Sager, and iTunes works great, totally intuitive, not a single problem.
This thing is the size and weight of a Bic lighter, sounds great, and no worries about dropping it -- it's ram-based and so light that I'm sure it could survive a hell of an impact and keep on playing. It's impossible to make it skip or hang.
The interface is great... I can put it in my snowboard jacket and work the controls THROUGH my jacket, no need to pull it out to pause, change the volume, or skip a track. The controls lock by just holding the play button for 5 seconds, so you don;t have to wory about accidentally hitting it.
You can set up a playlist, load it to the shuffle, then play in order or random (shuffle).
Set up different playlists in iTunes and upload your soundtrack for the day before you leave the house. Just plugs directly into your usb port, and boom, choose a soundtrack, upload in a minute or two, then it's good to go. Since it will hold about 240 songs, you're good for tunes for the next 16 hours, without repeating a thing.
I'm sold -- this thing, especially at only $150 (the great iTunes software included), is a great value.
The only downside: everyone else that wants one hates me, because they are almost impossible to get right now... the first batch sold out almost instantly...