Exposed rafter tail ends won't trim square

[GeneDavis]

I've got roof edges designed with 4x5 timber rafters on 32" centers, one false tail sistered to every other 2x8 rafter, the eaves cut square not plumb, and Chief framing won't trim the rafter end square.  The overhang parts of the roof are sheathed with 1.5" t&g decking, the interior part of the roof is OSB sheathing atop 2x lumber rafters.

 

What is the solution here?

 

An image from my Sketchup workout shows what is wanted, and a little test file done to proof the build specs is attached also.  I wanted to proof it before taking it to the big plan.

OH test.plan

[DavidJPotter]