Yes I am a Windows person, an MCP no less, but Apple have always made great hardware and the new iPod is true to form in every respect except that they are selling it for a reasonable price which is very unusual for Apple... so I bought one to replace my stolen Archos and its fantastic.

I think iPods are fantastic, but using iTunes for Windows was a huge dissapointment. Although it looks nicer than MusicMatch, and does better syncronization with the iPod, iTunes is missing so many crucial features (eg: decent synchonisation to a local drive, plus many more) that it was not very useful to me.

That dissapointment turned to mild rage when I tried going back to MusicMatch - it took several hours to get any other software to talk to the iPod after iTunes had been installed.

I had to uninstall all iPod related software (iTunes, MusicMatch, iPod installer and the iPod service), reformat the iPod and reinstall them all again, sans iTunes of course, to get the iPod working properly again. It also took several goes to figure all that out.

The thing that most surprised me about this software debacle was that the iPod software for Windows (iPod Manager and iPod Service) is a excellent example of how to write Windows software which is both user friendly and a good Windows citizen, yet iTunes managed to show none of that Windows programming prowess.

I have since installed ePhod to do the iPod synchronization (http://www.ephpod.com/), which is just fantastic and happily coexists with MusicMatch.

My recommendation are:
- rip CDs with MusicMatch (its the best ripper around)
- play locally with WinAmp (WinAmp with a few plugins is unbeatable)
- sync to the iPod with ePhod
- never use iTunes again

And thats my 2-cents worth.