Well, a, um, "literal" example was the initial occurrence of what I've just learned is called the "hamburger" icon/menu. Which was "backported" to Google's desktop designs.

A particular instance I recall was changes to the Calendar web page presentation. Mom initially struggled a fair amount with the controls in the left bar for selecting which calendars were displayed. This was in a Google Apps environment with 20-ish people participating.

I remember when screen presentations could be somewhat cryptic -- per your description as well as other instances. But, as you point out, there was usually a manual. Now? Often it seems to be down to guessing and poking around. Or asking friends. But if you are a bit older and not constantly talking over such things with your friends, that means of edification is somewhat starved.

P.S. Thanks for the response. And as I said, I'm curious about the perspective of someone on "the other side". I'm not trying to be unduly critical, here; just, this is an issue I've consistently bumped up against, from my own perspective.