I'm amazed by the smooth transitioning and updating by iTunes on my two iPods and my iBook. I've done some minor equipment upgrading and maintenance lately, and it's been trouble free. 1) I have a 4th gen G4 iBook with a 40g harddrive. My music was taking up 17gig, so I pulled a 40g HD out of an old Compaq pc someone gave me, ordered and enclosure for about $30 delivered, hooked it all up, formatted it (7 wipes = 11 hours), moved iTunes (article here and converted my larger MP3s to 128kbps AACs. Had a few issues with song duplication, but nothing a little leg (or finger) work couldn't handle. 2) Wife bought me a 5g 30gig iPod, so I had to look up how to run multiple iPods on one computer so she could have my 4g 20gig. A quick search on MacRumors led me to this article at the Apple support site. I could just update both iPods with my entire library, but there's so much my wife won't listen to, so I've created a playlist for her. Easy...!!! 3) FINALLY (after a week) had the guts to delete my original iTunes library on the iBook's harddrive. So far so good with the old harddrive in the new enclosure. I now have 40g of free space to play with: 20g on the enclosure, 20g on the iBook. It was fun just now plugging both iPods in at the same time and watching them update simultaneously. Try that on any box running Windows OS...I can only imagine the loss of time, music, and sanity. iTunes even knows my 5g iPod is black, and has the little black iPod icon, and my wife's white iPod right above it! So cool! 16 months a Mac user, and never more pleased and excited about my equipment! Merry Christmas and/or Happy Holidays fellow Apple lovers!