I often find official documentation difficult to follow, and generally find myself on "other" sites looking for 'real' examples. I'm sure there are others who are the exactly the other way.
A living document with real world examples would answer questions I've had and many questions I've seen. Would you still have people asking questions that are 90% the same as something in a document and only 10% unique? Yes, but answers to those questions could increase the quality of the documentation. I might add an answer on topic x, but not have a complete understanding of the topic. Yet still I could contribute a good example to the document, or someone else might take my answer and decide it worthwhile putting in the document.
As for keeping things up to date, perhaps something like tags for version numbers. So you could search application + ver + search term. When a new version is released a tag just gets added to say yes this is still how it works for this version. If it changes, a document is created with the changes and the new version added.