The point is that Apple is devoting time, money, and lawyer- and engineer-hours to breaking your iPod and selling it to you as a "fix."
Imagine if your mobile phone manufacturer enlisted your car maker into ensuring that you didn't use a third-party charger with your cigarette lighter, but instead bought the official, expensive licensed charger. Every time you take your car in for warranty-mandated service, the manufacturer's representative rips out your lighter and puts a new one in that locks out your charger. And when the agent is done, he smiles and tells you he's "updated" your car.
Does the fact that you can go out and find a new third-party charger that works with the new lighter mitigate in the car-maker's favor? Wouldn't you be pissed off that your car-maker was selling you out to the phone company, treating you as a mark to be sucked dry by whatever vendor it decided to do a deal with?
That's what Apple's done here. The music industry has concluded that it can maximize its profits by restricting what you do with your music, and it's signed Apple up to see to it that even if you figure out how to do more that Apple will do its best to take that feature away from you.
In any event, there are many tools to help get your music off your iPod. Here's a link to Open Pod, the one that I've decided on. It's a GPL-licensed tool and looks like it works well. Link (Thanks, Jeff!)
I write books. My latest is a YA science fiction novel called Homeland (it's the sequel to Little Brother). More books: Rapture of the Nerds (a novel, with Charlie Stross); With a Little Help (short stories); and The Great Big Beautiful Tomorrow (novella and nonfic). I speak all over the place and I tweet and tumble, too.