Up until recently, my family was still stuck on Windows computers and the sharp contrast between configuring my own Mac and their Windows PCs was striking. The issues I had put behind me after switching during the Tiger-era were now apparent again and it was a wonder how anyone put up with such BS.
Family friends and other non-tech-people would share their horror stories of how frustrated they were with their Windows PCs from XP up to Vista. These people were the epitome of the average customer and were not interested in computers in any meaningful way and yet their topic of conversation would frequently steer to their recurring frustration with Windows.
Apple products on the other hand have always received nothing but platitudes and praise after friends and family have switched. "So much better" is something I've heard frequently after they have bought their first Macs and iPhones.
The opinions of each brand cannot be any more opposite.
Brands are a promise to consumers for what they can always expect from the product: Virgin stands for new, disruptive businesses, Southwest Airlines stands for no-frills air travel. Consumers know what to expect with brands regardless of deviation from the typical experience.
Windows is Microsoft's most important brand and since it's inception it has stood for a confusing, infuriating experience. The Windows brand has been extremely consistent in being rubbish and only recently has Microsoft actually attempted to address this.
Too little, too late!
A terrible experience is the Windows brand because it was rarely ever an acceptable product. The brand has reached the age of maturity in cementing it's consistent negative experience and consumers have moved on.
Microsoft can change Windows but they cannot change their brand perception.