NOTICE: I am bowing out of this thread. The OP has informed me via PM that he was tasked with this project by his employer. Yet he has no coding training nor experience. I do not have the patience to teach the very basics of programming let alone using the Ruby coding language, when they are free, readily available and are a prerequisite to learning how to apply the Ruby API extensions to creating SketchUp plugins. A classroom is a better place than a forum to learn these things.
As this task is an advanced programming exercise, it is my opinion that his employer should hire a professional freelance programmer. I am not willing to spend my free time taking work away from another programmer.