I started programming in DOS professionally in January 1991. It was pretty clear how bad Microsoft sucked by February of 1991, and blindingly obvious when they "updated" DOS more than annually with "95% backward compatibility" which translated to: "we just broke all your programs and you're only going to have to figure out which 5% of your code you're going to have to update to make it work in this version - aaaaand, by the time you do that we will be releasing a newer version! ;-P "

Something called DrDOS came along and we used it just because it wasn't updating and breaking backward compatibility so often. Since 640k wasn't enough for us even then, we ended up putting the kludge "Phar-Lap 32 bit extender" libraries on our product so we could access all the cheap RAM that systems were being shipped with (2MB was pretty much standard by 1992).

Then there was the day that McAffee decided that our product's main .exe was a virus. It wasn't. It wasn't infected with anything. It didn't do anything vaguely resembling malware. McAffee just had a false positive pattern match with our software.

The Microsoft treadmill was a very real thing all through the 1990s - much like Android and iOS are today. Sure, you've got a cool idea for an app, but we're going to keep shifting the OS underneath you so that you're spending 90%+ of your time just recoding your same old app for the latest OS release. That way you don't have any time to innovate and maybe threaten our business model.