They were accustomed to lightning fast internet on Macbooks and constant technological churn. Unfortunately for these exceptional people, poverty is logic resistant and nearly impossible to understand second-hand.
The tech scene's obsession with meritocracy is an extension of this.
I think this is giving too big of a pass to wealthy people. If wealthy people put in the effort, it isn't hard to understand the struggles that living in poverty bring. I think a better way of putting it is "It is very easy for those that have never lived in poverty to not consider the struggles that it brings". There is no difficulty in understanding, it is just easier to not every try to understand, so many wealthy people don't. It is a choice, though.
The security wisdom I've always seen was to use 2FA and prevent other attempts at authentication, but if Google is evil for doing this security... what's the answer?
Anyway, I think the the common case is that most data is recoverable with an ID or whatever they require. FWIW, searching HN for: “locked out of icloud” doesn’t produce much.