We've now been able to trick SketchUp now to pose TUIO data is SketchUp data by posting the TUIO data as a SketchUp "User" message type. It would then be in sync with SketchUp events rather than asynchronous TUIO events.
This way we can sub-class SketchUp ( like EventRelay ), pass the data off to the SketchUp's embed Ruby as a Synchronous event. Here's the result of DLL "puts"-ing cursors successfully to the SketchUp's embed Ruby Console via a Ruby API puts statement
Implication to which is that we can collect all the TUIO messages and use the SketchUp Ruby API for remaining work as suggested by mentor.