"To install an OS update? We're not talking day to day use here."

Correct. There are different ways this can be done but basically if you are using an enterprise management tool like System Center, it's all automated. In fact, you don't _ever_ need a monitor, not even for the initial OS install. Just plug the server into the rack and power it on. The server will auto-discover, install the OS, and become a host (or whatever you want, it's obviously fully configurable).

Microsoft has tens of thousands of hosts in their data centers that get updated all the time so obviously it's not practical to have a guy with a crash cart walking around doing it manually.

The same applies to Windows desktop machines. And with Windows 10 it can all be cloud based (instead of a on-prem System Center implementation). Keep in mind, Windows10 is a massive IoT play for Microsoft and IoT devices rarely have "heads".

This is obviously off-topic for this list so my appologies. If anyone wants more details please feel free to contact me off-list.

John