Dave just had an awful iTunes experience:

Arrrgh, I plugged my new iPod into my old Mac and lost everything on it. Never got a confirmation dialog asking if it was okay if it wiped out the music and audiobooks that I painstakingly took hours of my time to set up. Never mind that the originals are on the other side of the United States. Honestly, how dare they design software that's so brutal?

More...

Now I too just bought the 60 gig iPod Video.  And its a lovely device.  The odd thing though is that on Windows there is the confirmation dialog that there doesn't seem to be on the Mac.  Interesting.  My main problem with the iPod on Windows is that it doesn't seem to download and synch podcasts correctly.  For that I turned to iPodder / Juice.  And, while I find the UI a wee bit confusing, it definitely rocks.  Last Saturday it downloaded hundreds of megabytes of Dave, Adam, Steve, Dawn and Drew and others.