> At each of those steps there were people decrying the loss of these things. Today however, most people don’t miss any of them.

Those statements don't really support each other. There's no particular evidence that Apple's timing was good, just that they dropped it and eventually nobody cared. But if they dropped it years before everyone moved on, then their timing was awful, not great, even though the end-state was the same.

Flash is a particularly weird example since Flash on mobile largely never existed, so claims to "drop" it are nonsensical. You can't drop that which didn't exist. Yes there was a brief attempt at Flash on Android, but that came long after the iPhone.

Dropping flash on desktop would have been a better example, but Apple didn't actually have the courage to do that, at least not on their own. It was more a unified push by all the browser vendors combined with Adobe themselves dropping support for Flash.