[corresation]

Because it's too easy!

I have to disagree. Windows Server has the illusion of ease, but the same mechanisms that guide your hand in the early days turn into a major hindrance later on. There isn't a Windows server running anywhere that doesn't have event logs jammed full of potentially deadly warnings and errors, and most "easily" setup Windows servers are setup insecurely and wrong.

In my personal experience (and I have a lot of experience with both) I've always found Linux build outs much more predictable and easy.

As to the "counter culture", that goes back to when Microsoft really were the pricks of the technology world. They've gotten much better, but it's hard to shake that.