A while back I got into a conversation with Daniel Hurtubise at Renzo Piano Building Workshop about possible Dynamo use cases. It turned out we had aligned ideas: Trying out different randomizing techniques with Revit Planting (and other) Families.
Today I recorded a short video demonstrating how you can do this in Dynamo. For the method to work you need parametric planting families. I got mine from Revit legend Andy Milburn. Read about (and download) my revised families in my blog post Flat People. Planting Families are a bit weird in Revit, but Andy made them flexible by using Family Nesting and Number Parameters for width and height scaling, in addition to an Angle Parameter for rotation.
This is a generic workflow that can be used on any number of Revit Families and Parameters. For instance, I have randomized facade modules with the same methods previously.