Yes, this is my first iPod so I am a little confused by it's user interface. So far I got iRiver mp3 player. It was small and light enough to use it in a gym. I did not have a need to carry my entire music collection to the gym with me so I did not bother buying iPod. Nano seems to be good comrpomise, it has enough storage capacity, it's small and light and it's iPod so I expected to have plenty open source solutions for it under Linux.
I just tried gtkpod and it was huge disapointment. I guess I got very old version but still it could not read iTunesDb file properly. I tried it before iTunes on Windows so later I noticed that interface is very similar. I do not like flat list representation of entire music collection. I find tree interface more intuitive and easier to navigate. I think I am too Windows-centric to appreciate iTunes UI ;-)
As far as iPod device is concerned I need to get used to wheel. It's too sensitive for me at the moment. I got same problems with laptops with touch devices so I am not surprised. I need practice. Also I t looks like I need to fix ID3 tags in my collection of mp3 files. It looks like file names and directory structure is completely irrelevant for iTunes so now I just dumped large load od unorganized crap to my iPod and I do not like it.