I don't think the OS is the problem. First, macOS went through PowerPC -> x86 -> x86_64. Secondly, iOS and macOS share a lot of components, including the kernel.
More difficult would be moving the app ecosystem. Apple could do PowerPC emulation with Rosetta, because Intel CPUs had leapfrogged PowerPC by quite a wide margin at that point. It's probably a more difficult feat to put off with x86_64 -> ARM. Though, I think Windows ARM (at least) does x86 emulation.
That said, Apple has a lot of leverage with/over the ecosystem. Most macOS/iOS developers are already used to having to fix their applications for the next macOS/iOS iteration, so Apple probably won't have much trouble convincing developers to add ARM as a target.
However, if this happens, we'll probably have fat binaries for some years again. For backwards compatibility, but it's also likely that they are not at the point where they could replace the Mac Pro yet.
It would be smart for them to do the transition though. They would not be dependent on Intel's cycles and product decisions anymore.
Here's a recent rumor summary: https://daringfireball.net/linked/2020/02/24/mck-arm-mac-202...
With the key motivator being:
> The reason for Apple to move Macs to its own in-house ARM chips is much simpler than that. (1) Apple’s laptop chips are better than Intel’s — they’re faster and more power efficient. (2) Using their own chips puts Apple in control of its own timeline for product updates. Why did it take so long for Apple to get the retina MacBook Air out the door? The one-word answer I was told by a high-perched little birdie: Intel.
If you think Apple doesn’t have macOS running on ARM today, then you’re probably missing something.
The transition will be harder for third party devs, but there having been popular ARM Apple platforms for over a decade will speed things up considerably. Many Mac apps will have ARM versions available overnight.
See, e.g.,:
https://www.theverge.com/2020/1/28/21100071/microsoft-surfac...
https://andregarzia.com/2019/12/a-week-with-the-surface-pro-...