When you say that "going away from the GUI was either the mark of doing something the hard way or because of a specific failure", it's true about windows because the windows command line was basically unsupported territory.

The Windows command line ecosystem was a stagnant ghetto for a long time.

You had to use an uncomfortable and ugly program to access it and the environment itself barely moved from DOS.

PowerShell was the first real progress in a long time and now they've arrived at 'lets just run bash on windows'.