I haven't yet set up iTunes Match and I would love to do it. The issues is... I don't know the origins of all my music... My music collection starts from back when I was in college and my ex bf used to make mix CDs for me which I then put on my computer. Looking back at it... I have no idea if those song were legit and don't even know what songs they were now. Also, he used to use my computer and may have downloaded music to it. There stuff on there I never listen to... And that I don't remember putting on there. I guess I could delete what I am sure I don't have the discs for etc... But I know I'll never get it perfect. What would you do?