Regarding #1: "Taking their beautiful hardware and subjecting it to Windows users must have been controversial inside of the company. It just didn't seem like something Jobs would do." -- Having read Jobs' biography, it wasn't something he would do: he argued against it, and even said that Windows users could use iPods "over my dead body." However, business sense prevailed, and Jobs realised that it made sense to open up the iPod world to Windows users.

Jobs was a proponent of porting iTunes to Windows, but Schiller didn't want this. As a result, Apple joined leagues with MusicMatch, and they made a music player, but Jobs said it was a terrible piece of software:

"To make the iPod work on PCs, we initially partnered with another company that had a jukebox, gave them the secret sauce to connect to the iPod, and they did a crappy job. That was the worse of all worlds, because this other company was controlling a big piece of the user experience. So we lived with this crappy outside jukebox for about six months, and then we finally got iTunes written for Windows. In the end, you just don't want someone else to control a big part of the user experience. People may disagree with me, but I am pretty consistent about that."

So Caldwell appears to be right in both points: it was understood that it would bring a lot of value back to Apple, but it also took a lot of smart people to convince Jobs to let it happen.