SSH is not even enabled by default on ec2. You have to Remote Desktop in, run a bunch of commands to enable it, and even then I could never figure out how to get authorized_keys to work.
Once you have SSH running, you can run commands via command prompt or powershell. Powershell is apparently pretty modern and well designed, but it's quite confusing if you're used to Unix.
A few applications I tried to install came as MSI's and they could not be installed via the command line, requiring the graphical interface.
It felt like a bad way to run a server. You want fast and lightweight remote access on a server, and you want scriptability. Windows was simply worse in this area.
Even if Windows was 100% compatible with Linux apps (including the modern CUDA deep learning stack...), I don't know why one would ever want to run Windows on a server. It lost the mindshare war, and I really see why. It really is that bad of an experience.
The main reason I've heard people use Windows server is because they are forced to because of app compatibility (no tech startup would find themselves in this position), or the preference of maintaining a server with clicking in the GUI (again, not a place most of us here find ourselves).
Anyways, I'd love to hear from someone, anyone, who likes Windows server more than Linux.
The point of this comment is also to state the opinion that Windows is currently a very bad Linux distro.