Can the iPhone sync with iTunes over bluetooth?
Curiously enough, no. I can sync my 4-year-old Nokia with iCal and Address Book over bluetooth, but not my brand new iPhone. I don’t use bluetooth headsets, so for me, the appeal of bluetooth is wireless data transfer. I expect this will be fixed in a future software update, however, and even if it doesn’t, it’s not hard to plug in a cable which you need to do for charging anyway.