What in the futhark is that ugly ass OS.

It was the first step up from Windows 3.11 which was basically a DOS GUI. It was rough, but definitely an improvement. Compare that to the latest "updated OS" from Microsoft now.

And 30 years ago it was quite easy to do dumb shit that completely ruined your system, be it in DOS, Win95, or OS/2.

Example from OS/2 - deleting the image file used for the desktop background in presentation manager (OS/2's core GUI) meant your system could no longer boot, and when you can't just google shit to sort things out, you were essentially up for a reinstall at that point.