Well, I had a Apple Laptop before I had this one (this one is a Compaq Windows 7) and I spent hours in the store transferring music and other stuff to a few memory sticks. I got everything except my videos and my music (and I had over 400 songs). I decided to get update my music, and replace a few songs. About a week ago, I deleted songs I didn't want or knew I wouldn't be able to find again (there was a small section that were randoms off Limewire, that didn't have proper titles).
If you want to get around downloading songs, go to
http://thepiratebay.org/ to get the file root, the right click and open in Frostwire (it's faster then Miro with Pirate Bay, and you get a direct link).
....just saying.
My grandma bought me a brand new iPod when my last one gave me a sad Mac. It was the last one that was pre-ordered before the real order for the city. I still have it, but now I never buy warranty.