IMHO The weird 16:9 aspect ratio really screwed us for usability. A 19" 4:3 monitor has the same height as a 23" 16:9 monitor. However I remember 1280x1024 being commonly available on games and on Windows by the time Windows 98 came out and earlier in games.
My brother had a 486 that I think I could run the game Mechwarrior 2 by Sierra at 1280x1024. The refresh rate went down to 60hz but it was doable and we didn't have a top of the line system even at the time (mid-late 90's). Here's a 1024x768 screenshot:
https://r.mprd.se/media/images/94067-Mech_Warrior_2_Mercenar...