Yep, that's the same issue with Mac. When you have a single Business Unit that wants Macs, they have to make a big sell to IT to get it. It's got to make a massive difference to their productivity for IT to absorb the extra effort for them.
Then when you return the costs to the BU they complain they have to pay more for IT than other BUs. Well, yea, you take more effort than everyone else who fit the standard model. Uniqueness ain't cheap.
It's usability issues in Enterprise (or just using Windows Pro on a domain with proper management) aren't the same as Windows Home.
And if OP thinks Windows has usability issues in business, let's see what happens when we replace 1000 Windows desktops with a random flavor of Linux.