Little bit further along, I am really trying to move this from Rhino3D into Illustrator to keep the vector detail intact. Illustrator has the Perspective Grid Tool so right now I'm just playing in Rhino to come up with the draft, then do it in Illustrator.
-----( new step here, little more detail )-----
Just finished a (PDF example) of what I want to do in Illustrator. Learning more about the perspective tool which makes positioning and transforming the top down view easy. Positioning the grid on the other hand is a little counterintuitive in several ways, the main one being that instead of adjusting the persp grid to the artboard (limits of what gets saved or printed), you should create the persp grid how you want it, and then edit the artboard until it encloses the grid. Then you turn off the grid, make sure what you want to be transformed is all grouped nice and neat, and after making the persp grid visible and selecting the view (left, right, top) you want to transform to, drag the object into the grid. Illustrator will transform it so it aligns with the view you picked and then you can size it, move it, etc, and it keeps that orientation.
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