I’d be interested to know why you chose Windows Server.
Nothing against WS, I work in that group, it’s an awesome product. Just curious about the reasoning.
Microsoft recently announced Nanoserver, a minimalistic deployment configuration for Windows Server 2016. It is explicitly designed for headless systems, there isn’t even a GUI. 10X to 20X smaller, fewer patches, fewer reboots. It is obviously not designed for this purpose, but I’m sure some clever people will investigate, just like in this article.