Luther went to jail because he broke the law. Reddington was a criminal not a cop. The Strike Team all went to jail because Mackey sold them out to save himself. Gordon resisted breaking the law until the government actively turned Gotham into a prison.

These are not great examples of a real problem.

MS did a shift like that already. The shift from MS-DOS to NT was transparent to the vast majority of people to the point that most people didn’t realize they were two different OSes.

I don’t see why they couldn’t do it again. NTVDM was similar in concept to what wine does. Imagine if MS actively contributed to wine, or a wine like project.