This would be an incredible amount of data to store. Already the burden on systems just to handle the volume of music and video sales is imense. To add snooping to this would be crazy huge.

I'm skeptical.

*note: obviously I know nothing and am trying not to speculate. I will say that there are often initiatives to make it easier and more natural to purchase stuff, but I've never encountered such an initiative to do things that are invasive or to track where users have been. Apple's more keen on showing you what you want than in finding out what you want.

If anyone is paranoid about this, they can always use iTunes offline, or use their iPods for listening I guess. shrug. I'm not that paranoid. This just seems incredibly infeasible.

It might also be worthwhile to check the iTunes EULA. If snooping is going on, it would be mentioned there, I would imagine.