Custom Shape Map (JSON) + Flow Map + Icon Map

Would really appreciate any guidance on a map visualization we are wanting to creat.

Currently, we are able to (separately) plot lines on a map showing Origin to Destination, using Flow Maps. We also have a customer JSON Shappe Map, where we display peformance by geographic region based on color and saturation. We would like to be figure out a method to:

1) Combine the plot lines Flow Map, with the custom Shape file, and

2) Add in a layer of icons from Icon Map to display physical client locations.

Is this possible with Python or something else? Anyone have experience with something like this?