Ironically using author Dan Cederholm’s SimpleBits as a test case, Tomas points to the W3C Outliner version of the site and reasons that perhaps there’s a more logical way.
And after seeing it visualized, Tomas seems to have a strong point. Without the outliner view though, in authoring mode it’s hard to make these sorts of choices correctly. Best intentions don’t always lead to proper choices, as evident by the case studies he links (including this site).
What’s particularly frustrating is that the spec itself doesn’t offer clear guidance on semantic issues like this; we are given overly simple usage guidelines, and actual implementation is left to author discretion. And that leads to confusion and individual interpretation of the specs by those who didn’t write them. We’d be hot and fast on the case of a browser vendor who took liberties in implementing the specs; why should content authors be any less accountable?
Anyway, the issue at hand is headings and there are a myriad of possible opinions here. The outliner appears to offer a firmer guideline than the spec, from a W3C voice, so armed with this tool perhaps we can move the discussion out of the realm of personal preference, and toward something more precise. Commentary follows at Tomas’ site.