http://www.metafilter.com/142475/Standard-flavored-Markdown#...
Yes, ambiguity is a feature in this case. Markdown was designed from the top down by a writer, for writers. This gives it the rare characteristic of being intuitive to understand and use, but not necessarily easy (or even unambiguously possible) to implement. The lack of a standard helps keep people honest by making them follow the spirit of the law, not the letter, as you see happening with things like HTML and CSS. In fact, I'd argue that's the entire philosophy behind Markdown: usable and understandable by ordinary humans, all the way down to the spec. (Ever try reading the C spec? It feels like you need a PhD to get anything out of it.)
I'm with Gruber that Markdown is successful because of its ambiguous (read: easy-to-understand) design, not in spite of it. The proof is clearly in the pudding. My feeling is that the people running into edge cases are trying to use Markdown as some sort of replacement for HTML, not a massively simplified syntax for writing articles and pages.
What I see here is a group of developers who arrogantly think that they know better than Gruber what to do with Markdown. They could have called it anything else, but they chose to make the issue political. It's juvenile, especially coming from people who we're supposed to look up to in the tech community.
According to Gruber, Markdown is the hardest thing he's ever worked on. He didn't spend a week on it, the idea was not obvious, and its success was not accidental. If I was him, I'd absolutely be seeing red too..