ParkingPsychology

I still have to log in via fucking RDP to set it up.

Nah you don't. I've made plenty of headless installations for windows. You think everyone with a datacenter with hundreds of windows servers logs in to each of them with RDP? You can do it with an unattended.xml file. Which is harder to do than what I had to do to make a headless raspberry pi ubuntu server. By a lot, although if you look long enough, you might be able to copy someone else's unattended.xml.

Also, Windows Event Viewer still blows

Yeah, it's... an acquired taste. You can actually script it. But it is harder than string manipulation, since the events are all objects, not strings.

Then why has every Windows admin I’ve ever had to deal with use the GUI?

Cause I'm lazy.

This is more about your windows knowledge than windows. All the stuff you're mentioning can easily be done remotely with powershell remoting.

Also, I often just SSH to windows servers. Works fine, has been like that for years now.

https://learn.microsoft.com/en-us/windows-server/administration/openssh/openssh_install_firstuse

That's probably 150 aborted campaigns totaling 900 hours and two completed 25 hour each campaigns. Source: I'm at around 1500 hours, maybe 2000. A lot of it predates steam, so I don't know exactly.

I've only completed one campaign ever. At some point you know you've won and you're just steamrolling. So why bother.