LOOONG time windows user (20+ years) making the switch over with a new iMac 24". Arriving today...woohoo! I've been reading up on the basic file transfer. I have an external drive that I'm loading up, but my main concern is getting off to a clean start by importing the files right the first time. I screwed up an iTunes transfer once (PC to PC) and when dealing with 40gb of music it is a PITA to cleanup afterwards. iTunes - I have a backup of my library. Any suggestions for file structure or where to put the files when I copy them onto my mac? I want to maintain playlists and start with a nice clean install so I don't need to go rearrange things later. Photoshop Elements - I backed up my catalog (30,000 photos). What is the best way to get these into iPhoto? Will they retain my categorization and version sets? Would it be better to import the backup or the file structure that has date stamps for folder names? Thanks for your help. After 28 years of computing I don't think I've ever been this excited about a new piece of hardware. That says a lot...that first TRS-80 when I was a kid was sweet!