They had good PR with businesses but I don't think they really cared much about the opinions of end users. When the overwhelming majority of computers sold come preinstalled with your software you don't really care if people dislike you. I think for many people (even today) Windows is just something they need to use the software they want. Chrome is getting there too, with more and more websites requiring it to work correctly.

When your audience is captive you don't have to pretend to care anymore.