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Revalidation with the option "outline" showns no result, even if a proper outline exists.
See Discussion: http://lists.w3.org/Archives/Public/www-validator/2006Oct/0084
The outline is now fixed in the maintenance branch of the validator codebase, with a release within the next few days. I am also confident I have found a way to not lose it even with the new architecture used in the development version of the validator, so the feature should not be at risk any more. I still recommend the semantic data extractor for outlining, and more tests of the richness of markup used: http://www.w3.org/2003/12/semantic-extractor.html