It's probably just my biases showing, but I never really found a Windows music player I really liked. They were either butt-ugly (WinAmp) or resource hogs (Sonique) or retarded (Windows Media Player) or expensive (most of the others), and none of them had the seamless library handling I was used to. I now have a Windows audio player I'm comfortable with.
I downloaded it at work, and then copied a few of my purchased tracks from home (Mac) to test. After "authorizing" the PC, they worked fine. The interface is pretty much identical. One really nice thing is that it supports Rendezvous, so other iTunes users on your local network segment (Mac or PC) can share their libraries and playlists.
I've been manually syncing my libraries using the doohickey. I'm thinking that you could do some amusing things with
ssh that would make the process even simpler, at least for the microscopic subset of folks who like to pretend anything involving cron jobs and shell scripts is ever really simple.
Always draw your curves, then plot your reading.