I'd be "unsatisfied" because a slow processor, a 4GB RAM maximum, and a shitty GPU would suck, sure. I upgrade and sell my old machines on a yearly basis or so because paying a $300-$400 delta (sell the old one, buy the new one) is worth it to have something in the target area for Apple and for developers. There's no point for me in keeping older devices long-term because nobody really targets the trailing edge. I spend more on car repairs in any given year than I do on my laptop upgrades; it is just not a significant amount of money.

If "people who keep old stuff" was what he was really going for, he's doing poorly at describing it, because I don't think that "long term customer" doesn't mean "customer who refuses to upgrade for geologic eras" among reasonable folks. And I certainly don't think an ecosystem where newer devices are generally preferred is a symptom of "bad engineering"--more "engineering decisions he doesn't like." Every MBP iteration has made me much more pleased to actually use the machine, and that's the core of what matters.