I just got the first layer of system working!
It takes and address, gets the google streetview, identifies all of the trees, then erases them so that the house is not obscured.
I'm planning to use this to build a service that plots the perimeter of the house and all of the trees relative to the perimeter.
Then we'll use any photo associated with the house to assess every tree, bush and object and provide the owner with guidance on how to harden their property from wildfires.