The thing is, this isn't a first-time user. The guy in that video is a Windows user. The expected learning curve should be short and shallow, because he should theoretically be dealing with incremental changes and not a completely alien system.
But he's sitting down at a new version of Windows and using it as if it were his first time using an alien OS. In other words, the metrics are completely at odds with what should be the expected learning curve.
What criteria are you using to determine an appropriate expected learning curve?
Is an operating system upgrade supposed to be like transitioning from a 2008 BMW 3 series to a 2011 BMW 3 series?
Or is it o.k. for the learning curve to be like transitioning from a 2008 BMW 3 series to a 2011 Dodge Grand Caravan where the brake, accelerator, and steering wheel remain the same, but all the other controls, the instrumentation, and cabin layout are different?
Any change has a learning curve which can feel steep at first. I've personally experienced it when changing browsers among IE, firefox, chrome, and Opera (never mind mobile versions) even though they all pretty much work the same way.
And my father makes the same face when he has new email from someone he doesn't know.
If you've made such a transition, you will find you have to adjust to the headlamp controls moving from the right side stalk to the left side on the console and being replaced on the right side stalk with the wiper control which is on the left side stalk in the other car.
Seat controls, speed control, radio adjustments, door lock operations, etc. all also change.
Not to mention that you can't get a Grand Caravan with a clutch and no sensible person would get a slush bucket in a 3 series.
Disclaimer: MSFT employee working closely with Windows 8
I speak as a former programming team member from a very high ranking school in the SE Region according to the ACM International Collegiate Programming Contest regionals.
"He's also been primed to expect a difficult task by his annoyingly condescending son. I'm not at all surprised that he struggled with it."
This has an enormous effect on a person's ability to solve problems. I learned this one day speaking with one of our coaches. I took what I recall to be a 1000 or 1100 point TopCoder Level 1 problem and told him it was "easy". I was being sarcastic, but he took me seriously and efforted more at the problem because it was "easy". He even postulated a few theories on how to solve the problem in our conversation. He said the reason he even did that was because I told him it was easy. Had I said it was hard, the results may have been different.
But he's sitting down at a new version of Windows and using it as if it were his first time using an alien OS. In other words, the metrics are completely at odds with what should be the expected learning curve.