Actually the iPod was late to market. They saw an existing market, applied their Human Interface Doctrine to it, determined what was needed to create a killer device and executed it to the letter. Jobs does not allow the engineers to give up when faced with the "impossible". He does not settle and pushes till they figure it out. Inovation is not about compromise.
The timing on the phone could not be better. The US lags the rest of the global market when it comes to the cellular space and emerging technologies. Asia 1st, Europe right behind them and then sooner or later the US.
A year ago a phone like this had no place in the US market, lack of hi speed infrastucture being the biggest barrier to entry.
Cingular is a natural choice since they are aggresively rolling out a real national 3g network.
In terms of the iTunes DRM I am continually baffled as to why people blame Apple for the restrictions. Apples DRM was the only way to get the paranoid record labels to buy into the iTunes Store concept. You can't sell the stuff if you have no rights and you don't get rights unless you protect the labels IP.
I'd guess that most of us here have some sort of cable service that comes with a set top box. If you try to grab the HD stream from anything other than public beroadcast you're out of luck. The signal is encypted to prevent copying. Blaming Apple is like blaming the cable operator who is relaying the signal and not the network that is actually sending the signal.
Digital Millennium Copyright Act
http://en.wikipedia.org/wiki/DMCA