I have been using iTunes for the last 1.5 years to buy Jpop versus importing it like I did 3 years ago. This action has forced (except for the iTunes Plus) me to use an iPod for a while, but after the most recent updates to the iPod line I finally decided it was time to leave. I don't like where Apple is going with the Touch and it is obvious that the Classic is just a stop-gap measure for the near future.
I decided to look at Sony, MS, and even Kenwood. I tried the Kenwood. It was great sounding, but I didn't care for its software.
I have used the Sony A808 and S703F. Both sound great (to me) but I am a bit tired of using Sonicstage. More importantly, I was forced to use software to transfer videos and pics as well. I know Sony has gone more of an "open" route here in North America, but I just don't know anymore.
I decided to give the Zune a new try and really like the new software and firmware (even on the old Zune 30). The only thing that truly bothers me with the Zune is that I still am looking at little boxes instead of Japanese and Korean fonts. WHY is it so hard to install 4 font files after more than a year of firmware updates?

Even with the "little boxes" nightmare, I have finally decided to stick with the Zune over all the other brands. The hardest part of the switch from Apple is converting my files to a non-protected codec as well as going back to importing my Jpop and Kpop. iTunes really did make buying East Asian music so simple and QUICK.