If you're looking for someone, I have iTunes purchases, and I'm not happy about it.
1) What are these magical capabilities you're talking about that are so egregiously missing from Android? At least with my Droid, I can download software to let me sync wirelessly.
2) When I get new music, why do I have to a) go through the steps of adding it to iTunes b) connect my iPad to sync c) connect my iPod touch to sync d) connect my iPod nano to sync? When Apple's pushing us to buy all these devices, it would definitely be convenient to have it sync wirelessly (or even just sync the stupid folder in iTunes). I don't care if it takes long if I never have to invest any of my time to do it.
3) I don't see how iTunes purchases changes any of this?