So, just in case anyone else wants to try my AI test for themselves, here's the setup.
a mac app with a left sidebar — an NSOutlineView subclass. assume the view has a view controller and a class that handles delegate callbacks.
the outline view is set to "SourceList" mode. this is important.
the new feature is to have the default source-list drag-image for reordering rows — but a custom drag-image when the drag leaves the outline view.
that's it. easy peasy, right!!?