As a hardware company, if a huge percentage of your user base is still using a product you made five years ago, there are two schools of thought:

1. "Great! Our products are so well-made, stable and backwards-compatible that users do not have to upgrade."

2. "This is terrible. We have failed so thoroughly to innovate that people are content with using five-year-old technology."

It's not like Apple is unaware of virtues of #1, but as a company they are clearly in bucket #2. In five years, if 600MM users are still using the iPhone 6, I'm certain they would also consider that "very sad". I don't think Schiller and the exec team have blinders, they are just holding the rest of the PC industry to the same standard to which they hold themselves.

I feel like you're just exemplifying the exact opposite here. You're making a lot of assumptions about a statement that, in context, is pretty innocuous. For as much as you're saying that Apple as a company has these blinders on, I think you have just as much of an issue with blinders. The statement can be taken at least 2 ways. It's telling that you've turned one short statement into a generalization about an entire company.

It's not as clearcut as you make it out to be though. More often than not those old PCs effectively deny a whole bunch of people access to reliable and fast modern computing. In that sense an iPad Pro would be very well worth the price. Think hidden opportunity costs through crappy, unstable UX.

Unfortunately the real problem with Apple is that they are still somewhat on track of losing the "functional high ground" as "it just works" doesn't apply as much as it used to only some years ago.

I hear that MS Surface is actually quite usable these days, I don't have first-hand experience with it though. I would be interested to know as I'm feeling more and more inclined of not recommending Apple products to that cohort anymore.

But now you've changed the substance of the utterance entirely. He didn't say, "I don't understand why people use 5 year old computers." He said that it's "sad" that they do. And, when you believe that your product -- especially the latest iteration of that product -- genuinely improves people's lives, it follows that anyone who doesn't have it is 'missing out on something great.'

This controversy ranks right up there with the 'let's make her smile' bit from the iPad Pro announcement. Manufactured to create a story, but not impactful in any way.

This story is old as the world. "Qu'ils mangent de la brioche" - "Let them eat a cake", as great princess Marie Antoinette said upon learning that the peasants had no bread.

There is no support for that.

https://en.wikipedia.org/wiki/Let_them_eat_cake

There is no proof it was actually her: https://en.wikipedia.org/wiki/Let_them_eat_cake

She never told that.

That was fictional phrase written in a novel by one famous writer, and attributed to Marie Antoinette, in order to discredit her because those who did benefit from that.

You should contrast your sources.

I wouldn't say it's a bubble so much as they just aren't motivated to consider those viewpoints. Apple's products are high cost and high status, they have no reason to consider the lower end of the economic spectrum; that's not their market. It would be like Rolls Royce running radio ads in rural Kentucky. Yeah, many people there would probably like one, but they can't get one.