I think that there's a lot of criticism toward Gruber because his opinions are not a carbon-copy of the unified public geek opinion that you'd see on a site like Slashdot. I think it's refreshing to see a solitary source of Apple commentary in which the author actually attempts to understand Apple's motivations rather than blindly lambast them. Gruber is not afraid to criticize Apple (I've read dozens of criticisms of the app store approval process, for example).
And that's always been his attitude: The opinions from someone who is a long-time fan of Apple products and does not instantly overreact to every news story about them like most tech sites. You can't accuse someone of jumping the shark for consistently doing what they've been doing for years.