You got the association off: It's not brand -> generic, it's "user has a problem" -> brand.
For non-techie people (most users), it was always "my computer" or "my PC" until they had a problem with it and had to think about "Windows". So yeah, as GP said, "Windows" did already have a negative reputation and was viewed as a necessary evil.
Particularly when the iPhone was released, Windows Vista had just come out a few months before.
>Windows Vista had just come out a few months before.
Yes, I know, Vista == awful. But I can never think too badly of it because I live through Windows ME, And when I think "worst Windows OS" everything else just kind of fades into the background.
It's overall an improving pattern though, with every other version being a step backwards, but not as big a step as the one before. Vista wasn't as bad as ME, Windows 8 wasn't as bad as Vista. At the same time, Windows 7 wasn't as much of an improvement on Vista as XP was over ME, and 10 not nearly as much of an improvement on 8 as 7 was on Vista.
Windows ME and Windows Vista were both terrible (it doesn't matter which one was worst), but that was because Windows XP and Windows 7 were also so good. So you start to notice the difference between the predecessor or successor which articulates the strong and weak points further.
For non-techie people (most users), it was always "my computer" or "my PC" until they had a problem with it and had to think about "Windows". So yeah, as GP said, "Windows" did already have a negative reputation and was viewed as a necessary evil.
Particularly when the iPhone was released, Windows Vista had just come out a few months before.