It is easy to setup a headless system - users do it all the time - hackers even more often.
Take the example here [root tip] [How To] Install Raspberry Pi - VNC over SSH and adapt.
If you want to remotely control your windows without a monitor the initial setup will require a monitor or a crash cart adapter - Crash Cart Adapter - USB - Video Capture - KVM Switches - but you would be able to enable RDP and use remmina or krdc with freerdp to control the box without a monitor.