Gruber seems to be right an awful lot for someone so casually vilified. For example, he took a lot of flack here for defending Apple's move to leave flash out of mobile safari. I think enough time has passed to make clear that he and Apple were right.
The anti-Gruber hate looks more like sour grapes every day.
Another way of asking this question is, can you name three times that Apple and Gruber differed, but Gruber was in the right?
Apple did eventually retire the brushed metal theme and is getting a bit more consistent in the styling of their applications. Still some way to go here, too.
Apple and Gruber has generally diverged in how they think the Apple Human Interface Guidelines (HIG) should be applied. Gruber has called them out for not applying it as consistently as they did in the past.
But regarding the HIG, it seems Gruber has resigned and is now calling the HIG basically defunct.
I think in general, Gruber is not trying to be right/wrong vs Apple, not trying to offer a strong opinion, except in some unusual cases (see: AppStore rejections). Mostly, he is just trying to understand Apple, and to offer his analysis since Apple is famously quiet and other analysts are often clueless as Apple is a bit of an oddball in the corporate world.
I can.
1. The App Store approval nonsense. 2. The missing white iPhone. 3. Software patents. 4. He's also picked on design choices of Apple with iBooks and believes the Kindle app is better.
These have all occurred within the past year alone. It's fine there are those that disagree with Gruber but I find it best to attack on the merit of what is written and not his bias. It is the easy way out.
It's been much more than a year since Steve's blog post about how Flash is unneeded because of HTML5, and I am still waiting for the improvements in Safari so that Flash like functionality can be used in web pages. http://www.apple.com/hotnews/thoughts-on-flash/
I am not holding my breath though, Apple wants to push developers towards apps and not web pages, because they get to make money on every sale and also because it creates a lock-in for their platform.
Even the most cursory glance at real numbers establishes this as irrelevant. Apple's App Store revenues are measured in millions of dollars. Apple's revenues on hardware are measured in billions. They use the App Store to sell more hardware. It's infrastructure with next to no margin.