I know that there is some migration assitant, but there are relatively few files in comparison to what I want to bring with me onto my new Mac. All my music which is about 10GB. according to iTunes. All my videos, about 25GB and a few misc. PDF's and documents. Here is the problem. I have an external hard drive with a lot on it, 250GB out of the 500GB capacity. How should I go about getting everything onto the hard drive and OSX being able to read it? Also, currently I have a lot of duplicates in my iTunes library, how do I go about transferring a single copy of the song I want so that my Mac would read duplicates either. I hear that I have to format my drive, but I don't think I have enough free space on my computer to put all my files onto my computer, format it for mac, and then transfer every thing back again. I can do a few trips back and forth, that doesn't bother me, but this iTunes duplicate thing is something I really want to avoid. Also, once I transfer all my files from my windows pc to my mac, should I delete the files on my hard drive and then use time machine to make a proper backup?