The triangle is real[1]. Something's gotta give when a deadline can't move, and as we know from Brooks, software development speed doesn't increase linearly with more people. So it's primarily quality or scope that must suffer to hit a software deadline.
[1] - https://en.wikipedia.org/wiki/Project_management_triangle
Honestly the OS X itself (uhhh macOS now) is still fine, even with Big Sur and its weird iOS controls, however the other software is sometimes weird; but - let's say Numbers was never good and iWeb was always downright bad. And iTunes was bad in Jobs era and is still bad (as Music).
I however still kind of miss when native Cocoa apps were sort of good and not just ported iOS app via Catalyst or something. But whatever. I'm old I guess
this really is key, if you can do it
alot of companies though, are "business driven" which means releases and schedules are set beforehand, which makes this hard... (but if you can do it, its great!)
And no doubt a great deal of crunch time, their fair share of delays, some major messes and the occasional outright cancellation. And if I'm not wrong their roadmap is not public information.
I personally find it hard to believe that a large company can exhibit all those adjectives you list. Everyone finds this hard.
Do they tell you at the beginning of that cycle what features to expect? Or do they constantly work on features, and then at presentation time do a freeze?