However, last week (after a computer crash required me to find a way to recover my music library from my IPOD to my trashed harddrive) I found a little app called Ipod Agent (http://www.ipodsoft.com/ipodagent.aspx) . I started with it just getting back my music collection (which worked flawlessly), then moved on to see what else you can do with it. It enables you to sync your data from outlook to your ipod just like if you were using a mac. And the really cool thing, at least to me was the ability to sync rss news feeds and local movie times to my ipod so I'd always know what was showing if I get a spare few hours.
The best part about it is it's free.
This may be a little off topic for CGtalk, but I thought I'd share nonetheless.