You won't regret it Jim - it's THE most enjoyable music gadget that I purchased in a long time. You use iTunes to upload stuff to your iPod from your computer. It's not a drag and drop interface - iTunes is the interface. As far as purchasing music through iTunes - I haven't done it. I think 99 cents a track is a ripoff for mp3s. I'd prefer to buy the entire album - the cost is about the same and you get complete wav files. And it doesn't have the copy protection that itunes comes with. If you have to reformat your computer - you lose your tunes and have to purchase them again. Also if you purchase the album you can rip to mp3 at whatever quality YOU choose and still have the album to listen to on your stereo. Just my 2 cents

Kathleen