Thanks Dan.
So, per your suggestion, I started going through the libraries that require 'openssl'
and replacing it with Sketchup.require 'openssl'
It seemed to fixed one after the other, until I got this:
Error Loading File C:/Program Files (x86)/Google/Google SketchUp 8/Plugins/Light Stanza/lib/Ruby186/lib/ruby/1.8/i386-mswin32/openssl.so 126: The specified module could not be found. - C:/Program Files (x86)/Google/Google SketchUp 8/Plugins/Light Stanza/lib/Ruby186/lib/ruby/1.8/i386-mswin32/openssl.so
Sorry, had a copy/paste error a second ago. Fixed it.