depends... do you want to be confused? or do you want to be frustrated for hours?
The Zune is awesome, but it can be confusing as hell and a total bitch to upload music on... I got rid of mine in about 2 months.. traded it for a 60 gig ipod... which is super easy to use, but very frustrating if your itunes keeps fucking with your brain by either deleting your music from your library, or not allowing you to update your ipod whenever you want...
Personally, I like the Ipod because I just bought a Powerbook G4... If I had a PC still, I would probably still stick with the Ipod...
Plus, now that all my stuff is on Itunes, I would be far too lazy to put it all onto a Zune.. that could take days (being that my Ipod has at least 55 gigs of stuff on it..