It’s not that it hasn’t gotten better, but that the entire infrastructure that’s underpinning the GUI is simply completely different than what people are used to. And I’m not just talking CLI here, because the average Windows user likely doesn’t use that to begin with – it’s things like filesystem organization, software management, driver installation, configuration files, etc.
And it’s not that these barriers are insurmountable either, but they DO require a significant amount of cognitive effort that not everyone is willing to put in.