I have the real world experience and I stand by my position. It does suck and I can empathize and of course I can understand why you'd pirate the software but are you really going to try to tell me that it's not wrong? Can you honestly say that not paying is okay because the price is too high and you don't agree with the reasons why you can't run your dongle on a new OS? That's what it comes down to in the end. It's about not wanting to pay and disagreeing with the price. The fact that you know the dongle should work on your machine doesn't put you in a position to
know why they want you to upgrade. Anyone in that situation would have a knee-jerk reaction and jump to thinking its a corporate conspiracy and they're just gouging people. That's plausible. Or maybe there's a legit reason that you don't know. But in either case, no matter how ridiculous the experience is (and I grant you that the example you provide is very unreasonable) it still doesn't change the fact that someone created something of value to you, you want to use it above all alternatives, and you choose to pirate it which is wrong.
Suppose I go to the Apple store and I want a new MacBook Air. I have to wait in line for an hour. Then when I get into the store they've upped the price by $10k. Then, even after swallowing my frustration, I look to pay but all the checkout guys are busy. So I decide this is fucked up and just walk out with it. You'd agree that was a messed up situation but it's not okay for me to walk out of a store without paying.
The point is something I can't fathom anyone disagreeing with. There's a product. It has a price. If you want it you have to buy it. If you take it without paying that is wrong. How can you disagree with that?