Excellent thread!
2003 When the 3rd Generation iPod was released, I purchased it. Knowing I was getting one, for 3 weeks I converted all of my CD's into iTunes. I remember at night while watching TV, I would put 2 CD's in at a time and over and over burn, burn, burn. It was very tedious, but in the end I had something that carried every song I owned in the size of 1 cassette.
Since then, being the good geek I am, I had purchased every iPod upgrade released, selling the previous versions to fund them. I am completely impressed with how far we have come.