I have been searching for a basic strategy to simplify my experience with iTunes. I am getting tired of losing songs, getting duplicates etc.. My basic problem is lack of knowledge and not thinking like iTunes thinks. I don't mind losing some of my music, but the amount of music is getting crazy. To the most part 99% of my music is music I have originally brought in from my own CD's. Then over time I have dealt with a dead mac book pro, 3-4 PC's dying and now I am back to a MacBook Air, which I love, but.... music has been the biggest hassle. I basically have most of my music backed up on one hard drive now. Most of it has worked when importing it into my macbook air on iTunes... but then when I synched it with my iTouch more than half of the songs are now unauthorized. I am sure this information has been commented on a million times... but I am hoping someone comments on here's the best way to deal with all my old music with the least amount of hassles. Thanks. ps. I could care less if I lose some songs a friend gave me - I just want to get to my own tunes long after the cds have been tossed.