iPod works with Windows
http://www.apple.com/ipod/specs.html
I'm going to pickup one of these in the next week or so when CompUSA gets them in stock.
http://www.apple.com/airportexpress/
It lets you stream your music from iTunes on your computer to your home stereo.
I digitized all my CDs so I never have to look for a CD again. I still burn CDs for my car but Alpine and a few others are starting to come out with kits that lets you hook your iPod into your car's stereo. You can order a BMW with an iPod adapter now. Hopefully when I buy the new Vette next year they will have it available for the Vette.