2 areas: 1) Windows---slow as Hell; 2) The iTunes store is so disorganized no matter what OS you are using. I just gifted a song. I can't find a shopping cart or any way to pay for it and gift the song. Where's the shopping cart? Have latest version of iTunes. iTunes needs some help--it has become so bloated. Apple better be careful or they will be the new Musicmatch! And I used Musicmatch with my 5 GB Gen 1 iPod. Only choice then on Winblows!