Thank you for your responses.
I guess this all comes back to me looking for a way to quickly and interactively model in a Shaded perspective window. I originally created a post with several questions and realized a shorter post may be more helpful in getting a response.
I have since added a gif of a basic workflow I am attempting to achieve in Rhino - Modeling Quickly with Dynamic and Automatic CPlanes, a 3D Wall tool, and a 3D Hole tool