the thing with the zune is that, yeah, you can share songs with other zune users, but how many of your friends have a zune? none of my friends have them, i actually dont personally know anyone that has one. so for me to get a zune, one of the "cool" features wouldn't even be of use to me.
Originally I never knew which one to buy either, but I got a free ipod touch with my macbook and it's great. It get's a bit wacky sometimes, but nothing that doesn't take a minute to clear up by itsef. and i'm not complaining, it was free haha. But i really want the new ipod shuffle...
I always have my music on shuffle anyway

and it's so small xD
But yeah, i don't really like the zune software either. Plus, going to a mac store is so much nicer than going to a non-mac store (microsoft) xDDDD