LOL, with Linux administering you have all the same issues as with Windows, and most stuff you have to manage through the BASH or using a web interface. Either you know how to manage a cluster of computers or you don't, does not matter if it is Windows, Linux or Mac, same problem still.
Yes MS licensing is a nightmare, there are so many alternatives and combinations, and the full detailed information can be quite difficult to get your hands on.
Has anybody tried Windows Server 2016 Essentials? It is really really easy to use via the Essentials dashboard. The traditional Server Manager Dashboard is available too though, if one want be in more control.
Either way...Windows is getting really good, there is so much stuff going on behind the scenes that most users won't even notice. And I am not talking about some telemetry data or MS spying on you. MS spying on you is total BS, they respect your privacy. There is a lot of really good change in the core of Windows, including multiple added layers of security that are completely missing in Windows 7 because these features are not built into the core/kernel. ...and more security features are coming with each new edition upgrade because the Windows 10 core allows to do this, where older Windows don't.