Hi Mike,
My advice would be to go for Python for sure!
One of the biggest advantages with the RhinoPython is that you can acces and use the RhinoCommon API
Note that all of rhinoscriptsyntax is build this way.
I’m not sure about your proficiency with coding, but what helped me a lot was to scrutinize the rhinoscriptsyntax code by means of breakpoints in the python editor.
See this post that might help follow my route:
Another extra: here on Discourse support for rhinopython is easier to get as my impression is that more (active) users use it.
-Willem