All of the late '80s OSs were not designed to do what we need in a modern OS, they all realised it. Had the company that made Amiga survived they would have had to, at one point, throw out Amiga DOS and start again. Because the Amiga was orphaned it is a living fossil, a picture of where OSs used to be.
But there was no winning strategy, had the owners of Amiga spent their money on development instead of beer and chips it would have still ended the same. Likewise there's no path for Amiga to join Apple and Microsoft either, there's just no money and no will to do so and no company to do it if there was.