Why does iTunes have to suck so loud?

To get to the crux of this question we have to travel back just a bit:

Back in November I picked out 2 MP3 players and put them on Megan's Amazon Wishlist. The shiny new 8GB Ipod 4th Generation Nano in a gorgeous purple and the more economical but almost equally as nice Sony 4GB Walkman Video/MP3 player in a ( Read more... )