OK, well, I hope this doesn't make things yet more complicated but in that file both shapes are closed and both have the normal even-odd winding rule. The reason that the shape on the left doesn't fill is because it carries an internal flag that disables the rendering of any fill attributes. Designer would never create a shape in that state and nor would any of the modern import filters. I'm not sure why the old Acorn Draw filter creates a shape in that state.
Were you able to fill the shape on the left in Draw? Did it offer any control over a path's "IsFilled" flag? (I can't remember.)
Phil
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