Well, I've had an iPod since the 40GB g3 was the best one you could get. I was using iTunes before that, because I find it's the best way to keep my library organized (All those automatic things...just turn them off and do it yourself!) Problem is, now I'm locked into iPods, because I've spent probably 40 hours organizing, labelling, etc. my iTunes library, and really don't want to do it again! (Not to mention I have a ton of music in Apple Lossless now...) The Zune software has come a long way, and is really good now, and spec for spec, the Zune thrashes the new iPods. Slightly bigger, but not noticeably so, and it has a bigger screen. It has WiFi, wireless sync, sharing, and store, FM tuner linked to the store, higher resolution video out, and an unlimited download subscription service. Not to mention that nearly every audiophile site talks about the Zune's significantly better DAC and amplifier. If I were buying my first player right now, and not very much locked in iTunes, it would be a Zune.