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After a lot of measuring and guesstimating, I finally got everything ready for a revised print on a new version of the SmartiPi support. There was some bed adhesion failure, but the print was an overall success and the parts fit exactly the way I hoped they would.
You can take a look at the previous file here. I started down the wrong design path and had to reconsider my shapes and angles in the context of the case and Raspberry Pi. The new version cost $1.95 to print, so it also economized slightly on materials compared to version 1.