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I think the problem is with your Ruby version. Here's the response I got from @macumber when I emailed about this error:

this is likely due to the change of Ruby 2.0 version we had to make to match SketchUp’s version in 2015. You will now need the 64 bit MinGW version of Ruby 2.0. Also you have to use 32 bit version of Ruby to work with 32 bit version of OpenStudio and similar for 64 bit. Here is the version of Ruby that I am using with OS 1.6.0 (x64):

C:\Users\dmacumbe>ruby -v ruby 2.0.0p594 (2014-10-27) [x64-mingw32]