After installing iphoto 6, I couldn't copy photos and to my nano. I run 10.3.9, and copying still doesn't work with the new iphoto update. This used to work in iphoto 5. I also have installed linux, but I doubt that that would change anything. itunes optimizes the photos, but they never transfer. The 'photos' folder gets created on the ipod, but the ipod show no pictures. While I'm complaining, I'd like to mention that it is hard to give apple feedback for itunes, and took me a long time to find the entry form for osx in general.