Not all software are done with the same quality, whatever the epoch.

It was possible to work with Ada as soon as 1980 wherever high guarantee of reliability was taken seriously, for example.

And not everyone is Knuth with a personal human secretary in well funded world-top institution.

In 2000s, Microsoft which was already sitting on insanely high mountain of resources released Windows Millennium Edition. Ask your greybeard neighbour if you are too young to remember. While commercialisation started in 2000, it is the last MS-DOS-based Windows version and so represent the pinnacle of what Windows 9x represented, before the big switch to a NT inheritance.

As always, the largest advantage of the good all time, is selective memory. After all, people that can remember know they survived the era, while present and future never provided much certainty on that point.