He gets it

But being as he's probably a Lib too (as are most IT geeks), probably can't make himself recognize it.

Adam Pash, one of the founders of Lifehacker writes an article on the Ipad, and some of the other I-things that are locked for your own good.

Jailbreaking! And certainly the iPad will see plenty of hacking, but only because Apple requires you to hack the device if you actually want control over it yourself. Apple's gotten into the habit of acting like you're renting hardware. They've become the all-powerful, over-restrictive, ambivalent IT person in the sky, restricting what users can and can't install on their hardware.

With a device like the iPhone, most people slowly accepted Apple's IT state over time. Apple's stance is basically that their lockdown is for your own good—they're protecting us from unstable apps, pornography, confusion, and other nasties. And for the most part, it worked, right? iPhones have remained fast, capable, strong-like-bull, and extremely popular.

Hmmmm....remind you of any certain ideology?
How about this?

What's dangerous about the iPad is that it's much closer to a "real" computer than the iPhone is. If you dock it with the keyboard accessory, it really is just a sort of low-powered franken-laptop. And yet this is a computer over which you have absolutely no control. And the question is: If we all continue to buy Apple's locked-down products hand-over-fist (Jobs went so far as to talk about Apple as a mobile device company yesterday), what reason does Apple have not to keep moving forward with that model—a model that, to many, is defective by design.

Apple's saying to consumers: "Trade in choice for a guarantee that this will work exactly as we designed it to, and you'll never be upset with a computer again." Unfortunately there's no reason to believe the trade is necessary. At the very best, it seems like Apple's extreme and obsessive control over what you're allowed to run on the iPad, iPhone, and iPod touch is maybe delaying the point at which your software demands outpace the hardware, but even that is debatable. With the iPad, iPhone, and iPod touch, you're trading choice and control in exchange for unsubstantiated promises.

Like I said, he's kind of skirting around this huge nanny state that in one part of his life, he's for- or at least ambivolant about.
Then when it comes down to the same nannyism directly infringing on his life, he doesn't like it at all.
Maybe there'a hope yet in some on the other side letting real life change their minds?