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I think it's the problem with the compatibility between openstudio and Sketchup. And the current version OS 2.5.2 can only be supported by SketchUp 2017. If you install this version of sketchup, the plugin can be activated by the way recommended by Aron.
https://github.com/NREL/OpenStudio/wiki/OpenStudio-Version-Compatibility-Matrix
This link shows OpenStudio Version Compatibility Matrix.