Even the simplest things like text editor or using a command line will be disruptive.
The support staff is going to be overwhelmed.
So how is it that people can go from XP->vista->10->11 and not break the bank on retraining or from windows to MacOS but somehow anything else is impossible.
This is not an logically coherent argument against linux it's basically admins being scared of having their decades of investment into wintel ecosystem devalued.
The problem is that because your applications is windows specific your not comparing windows to linux your comparing whatever legacy mess of custom applications that people use to get their job done to whatever your replacing you win32/winforms legacy stuff with(which is something you have to do anyway as that platform is dying).
Windows isn’t dying anytime soon.
Just one, Microsoft Excel.
But I do use nano and not vim.