I've had both (iPod Mini, video, and 1G Nano) and I love my Zune 120 more than any iPod. For me, the menu system is easier and more intuitive. The software is so much better. iTunes tends to hog your system memory while the Zune software is lightweight and does the job. iTunes might be the easiest buying experience, but I don't believe in Apple's closed system. Their whole business model is to create a device that forces people to buy media through Apple. That's why the iPad is so genious. They've created a device that people can consume many types of media on...and, for the most part, you have to buy it all through their store - $$$. Anyway, I digress. As I stated previously, I do still use iTunes because it auto-manages my library file system and people sometimes give me iTunes gift cards as presents. The Zune software is getting better with each version. I'm hoping I'll only have iTunes to use the gift cards soon.