I can't say from the perspective of Unix to Windows, I'm the reverse, but I know that since learning to love apt-get (and similar managers), I'm willing to acce

I can't say from the perspective of Unix to Windows, I'm the reverse, but I know that since learning to love apt-get (and similar managers), I'm willing to accept chocolatey despite it's weaknesses. Just the other day I was able to update a whole load of software on my laptop using the 'cup' command - which worked almost perfectly. It broke my installation of Libre Office - which I then had to install the old fashioned (for windows) way. But that was still a considerable amount of time saved for me!