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Sorry for the confusion here - the documentation needs to be updated. (Bug filed!)

What's going on here is that we're trying to move OmniOutliner closer to the behavior of Apple's own apps. Specifically, we're trying to restore the state the windows were in when the app was closed, and if there are no windows, open a new document window for you.

There's one thing that TextEdit does which OmniOutliner currently doesn't - opening a document will also remove the unsaved document it auto-created for you. That seems a little friendlier than leaving the unsaved window hanging around as we currently do - I'll file a feature request on that.