Hi all, I´ve done some searching on this topic but still am a little unclear and want to figure it all out before trying anything. Can you experts read through my situation and offer any answers or advice? Thanks! I have all my music on iTunes on a Windows PC. I had a 4G iPod but it broke a few months back. I recently bought a 5G iPod and MacBook (will be arriving shortly). From what I understand, I will have to format the new iPod as a Windows iPod, then load it up with the music that is on my Windows machine. I then want to move all my music and put it on my new MacBook. It seems that there are two ways to do this... 1) Set the iPod to manually update, then plug it into the MacBook and drag the music over manually. OR.... 2) follow the directions at this link http://docs.info.apple.com/article.html?artnum=300173 which seems a little more complicated (e.g. looks like you have to copy your music twice onto the iPod??) First question - which is the correct or best way to transfer the music to the MacBook? I don´t care about playlists or playcounts, but I DO want to preserve artist and album info, etc. Second question - I want to use my MacBook as my primary machine in the future. Once the music is transferred over, will I ever be able to set the (Windows-formatted) iPod to Automatic synchronization again or will I always have to keep it on manual synch? Thanks! Sorry if these are dumb questions, but it´s a little confusing and I just want to do everything correctly on the new Mac!!