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I do think he was right to comment on Jason's speech / sales pitch @ Gnomedex; whatever followed from there I think kind of depends on how you read stuff from either side. Dave might sound like a jerk at times, but his approach, while being more abrasive, also strikes me as much more honest than the marketing-type speeches that Jason is offering up (although I admit that I haven't read everything from Jason on this particular issue).
I think Dave's talk at WordCamp was fairly representative of his style, and it does often piss a lot of people off, because he doesn't beat around the bush about stuff very often, at least when it comes to expressing his opinion on these kinds of issues. I think that style especially pisses off certain types of people (Jason being one) more than others, so it's understandable that there's going to be tension there.
The last thing I saw on this earlier today was when Jason asked Dave to alter the way he had been writing in his blog about this issue (or cease it altogether). Knowing Dave, how could anyone expect anything less than a very strong response in opposition to the mere hint of suggestion of censorship?
I do agree that it's fun to watch, though.
Winer's just seems cranky and very opinionated. Especially when it comes down to RSS and anything he "doesn't get". And he has it both ways all the time, while he hates facebook because it's closed he loves to use his iPhone.
He's certainly opinionated (which can be both good and bad); I don't know if I'd call him cranky, but I guess it's all in how you interpret what he says and the way he says it. Often people who speak frankly or abruptly are considered rude when they aren't necessarily trying to be.
At least from what I've read, I think he has the same position on the iPhone that he has on Facebook - he's commented quite a lot in the past about how he doesn't like the closed nature of either. The only difference is he also likes the iPhone as a fun gadget, in spite of its restrictions.