The thing that turns me off about Apple products is their reliance on iTunes to transfer music. I've always hated it and try not to use it. For my 1st gen nano, I ended up using Winamp and the ml_ipod plugin for drag and drop goodness and it was great. I recently put Rockbox on the nano and it's breathed new life into (after not using it for lord knows how long). I still hate the battery life on mine but I don't see myself upgrading to a newer one although the Ipod Classic looks great but again, iTunes can eat my balls.