I have a friend who just got a new MBP and she was having me help her set it up, which went totally smoothly until I came across an older iPod that had been configured for Windows. The iTunes screen keeps asking if I want to erase or to transfer and convert (I might not have all the terms down perfectly as I am not over at her place anymore, but this should give you the general idea). In the end, the point is that I cannot transfer the 300 songs that are on the iPod, even after we signed into iTunes under her Apple ID so as to ensure no DRM issues.
What next?
What next?