Bodybag : exactly how I felt! I mean, this player costs about twice of what it's closest competitor costs and even the most basic stuff (like maintaining a directory structure) it can't do.
Man, I've been spoilt by my Empeg. It's sad it's taken me another 650EUR player to realise that.

svferris :
thanks for your quick replie ! I can't believe I'm the first to report this!
You are correct when you state that copying files though explorer doesn't work. The iPod's FAQ clearly states that. It seems that a copy via explorer is only convenient when using the iPod in "portable HD mode", but not if you want to actually play the files.

I sure hope your engineers can fix this issue soon, because it's driving me absolutely bonkers. If they can't adress it in the next few weeks expect to see an iPod for sale in the "for sale" forum soon.
Stating that the system of the iPod is not as smart as the one of the Empeg is the understatement of the year. I mean, my NEO35 was smarter than that! So far my impression of the iPod is : nice package, but very little else. (I feel a dumb blonde joke coming up... )