The foundation for everything technical I know today began in MS-DOS 5, on a 486 with 2MB of memory. I skillfully tweaked my config.sys and autoexec.bat to make this machine run like a champ. Today, I too am woefully resigned to Windows 10 and all it's shortcomings.
And let's not forget, with version 3.11 it became Windows for Workgroups, highlighting the advent of local PC networking.
This was a great recounting of the painful growing pains of Windows, thanks for putting this together and sending me off reminiscing.