The "just jailbreak your phone" argument isn't useful in my opinion. It's an easy way to avoid the actually difficult questions that arise from what Apple has done with the App Store.
Would "just jailbreak your phone" be acceptable advice to give to your mother, who is always rolled out as the beneficiary of Apple's tight control over the App Store ecosystem, if she were to want to obtain the recently banned Readability app? If not, then we shouldn't be using it as a way to sweep these discussions under the rug.
It's not circumvention because it was explicitly permitted in an exemption.
HOWEVER, there's still a big gotcha: that permission does NOT exempt you from the "trafficking" provisions of the DMCA. So you're not actually allowed to "manufacture" or "import" a circumvention device.
In other words, it's a catch-22, where you're allowed to do it but denied the means, because you're not allowed to make or acquire the tools to do so.
As to the question about Apple, I don't like this move: it's sort of like they don't want people to let people know all the creepy things people can learn by knowing your entire social graph. But they have no trouble using that data themselves. I solve this issue the same way I do with Apple: I have no Facebook account.
EDIT: This article is about something else, but it has a pretty good explanation of what the DMCA means by "trafficking" and why it's so crazy:
It's possible that a court would exempt you from trafficking if your tool only worked for an exempted work, but nobody has tested this in court, so you do that at your own risk.
