I have a 60 Gig Ipod Photo. When attempting to sync with Itunes everything works fine unless I also check "sync" with Iphoto i get "unknown error (-50)". Ipod support had me just initailize my ipod and start over, which worked until i tried to have it update Iphoto as well. I only have 1.5 gigs of pictures in Iphoto and 27 gigs available. To really throw a wrentch at you it will upload pictures if a folder source is choosen instead of iphoto. Any thoughts?