Despite John being one of the two people behind Markdown (a pretty significant programming contribution), I see what you mean about him being in a "I don't have a horse in this race" position. However, I think that allows him to objectify a little bit more than others... I can almost feel the rumble of the laughter in the audience. Let me provide some examples.

John doesn't like the way the App Store functions in its current state, but he understands why Apple operates it the way they do. As evidence that he doesn't like it, I'll offer some excerpts:

http://daringfireball.net/2010/06/iphone_os_too_closed

Jason Snell: "All Apple needs to do is add a new feature, buried several menu items down in the Settings app, that mirrors the one found on Android devices: an option that lets you install Apps from 'unknown sources.'"

John Gruber response: "Personally, I’d welcome such a move, but I don’t think it would have the effect Snell envisions."

A lot of what John Gruber says could be interpreted as back-handed agreement, were you not to trust him. But the body of his writing suggest that he's genuine.

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http://daringfireball.net/2010/05/nack_control

John Nack: "The effect on product development and innovation can be chilling. Yes, it’s easy to point to 200,000 apps on the App Store; it’s harder to note all those that aren’t there — serious apps that will be created only if developers know they’ll get a truly fair shot to innovate and compete."

John Gruber: "I agree with much of this piece by John Nack today, regarding what everyone — developers, users, and even Apple itself — is missing out on because of Apple’s tight control and management of the App Store"

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Back from 2008: http://daringfireball.net/2008/09/app_store_exclusion

Fraser Speirs: "Apple’s current practice of rejecting certain applications at the final hurdle — submission to the App Store — is disastrous for investor confidence."

John Gruber: "Exactly right. If you only find out at the end of the development process that your app has been rejected — not for a technical problem that you can address but because Apple deems the entire concept to be out of bounds — then who is going to put serious time and talent into an iPhone app?"

John Gruber conclusion: "Either way, something is seriously wrong."

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http://daringfireball.net/2010/04/middleware_and_section_311

John Gruber: "I don’t know that Apple is right. As I said above, de Icaza’s perspective — that these decisions and risks should be up to individual developers to make — is utterly sensible. Siracusa is exactly right that this is a wager from Apple. Apple is betting its entire mobile future that their developer platform is better than everyone else’s."

It's especially evident that he's conflicted here. He doesn't necessarily agree, but he understands Apple's position.

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There are a myriad of other places where he's been critical, yet understanding of the forces driving Apple. What's concerning is that recently, John has been reconciling this conflict -- seemingly as much for himself as for his audience -- by pushing the Web Apps as an alternative approach. I'd love to provide a link to support that, but it's more of a tone than a specific rant.

Based on the nine occurrences of "Web App" on Daring Fireball right now, as well as the injection of some links supporting criticism of the lack of a robust Web App IDE, I'd suspect that a thoroughly vetted rant is in the works.