Update 1/20/2015 - even simpler solution found
Is it possible to use Corticon to generate an Org Chart like this?
Yes, Of Course! And in only two rules!
Corticon analyzes the relationships between the users and generates code that can be used by a program called Graphviz to draw the picture (http://www.graphviz.org/ ) Incidentally this is the same program that is used internally by Studio to draw the rule dependency diagram and the execution sequence diagram. See attachment for details.
Incidentally the data used for this org chart was read from the SalesForce table called "user" using Corticon's Enterprise Data Connector in conjunction with DataDirect Cloud. I'll be publishing a case study on this shortly.