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The Good News is that OpenStudio 2.0 (64bit) and OpenStudio 1.14 (32bit) with Sketchup Make 2016 (32bit) can coexist: If you install OpenStudio 2.0 first, and OpenStudio 1.14 (32bit) afterwards, Sketchup (32bit) will recognize the OpenStudio 1.14 plugin. So apparently it's the last install that determines what Sketchup is looking for.

The Good News is that OpenStudio 2.0 (64bit) and OpenStudio 1.14 (32bit) with Sketchup Make 2016 (32bit) can coexist: If you install OpenStudio 2.0 first, and OpenStudio 1.14 (32bit) afterwards, Sketchup (32bit) will recognize the OpenStudio 1.14 plugin. So apparently it's the last install that determines what Sketchup is looking for.for. This has been tested on my Windows10 computer.