If it had been a piece of shovelware I doubt they would have bothered. But there were some applications and games like this (Myst also comes to mind) that were

If it had been a piece of shovelware I doubt they would have bothered. But there were some applications and games like this (Myst also comes to mind) that were so main stream MS may have had them on a punch list of apps to test before a release. When a game or app is sort of a poster child for “why should I buy a pc?” they didn’t have much choice. For countless other apps consumers had to fiddle with voodoo HIMEM configs and other such things you might hear rumored on street corners late at night trying to work so binary magic. I’ve heard the Sim City example before and I think it gives MS entirely too much credit for being OCD on compatibility. Plenty of things simply broke.