Clearly there's massive competition in this space. I was about to ask you what devices you think come close or even exceed the coolness of the classic iPod. I have a friend(Tony Krijnen) sat next to me who's watching me type this post - as a result of the last couple of lines he handed me his Samsung Portable Media Center(PMC) - WOW!!!!!
I'm still really interested to get your feedback to the original question.
The Samsung (unlike some other PMCs) is small and lightweight AND has a decent size screen. What I REALLY REALLY REALLY like is that it supports VIDEO too. This is nothing new in the Windows devices but the size and weight of the other devices I've seen have ruled them out.
The other nice thing is that PMCs can handle my WMA (Windows Media Audio) music - my entire collection is encoded in WMA. To use an ipod I'd have to convert it to another format - it's a pretty straight forward process but still a hassle as I end up with two copies. I gather(correct me if I'm wrong as I'm hardly an iPod expert) iTunes likes to change the directory structure/filenames to make it easier for the device to search content.
Gimme some feedback - what works for you and why