I am using Model Builder to route water meter shut offs and services for a daily route. The output is an HMTL document with the directions. I have not found a way to add the map at each stop for the GP Tool located at Network Analyst Tools \ Analysis \ Directions. I know that you can add maps from the Directions tool on the Network Analyst toolbar, however I am trying to find this option on a more automated approach in Model Builder or Python.
The GP tool in Model Builder does not have access to the map document, so not able to add inset maps into the html output from the Directions tool. (The directions window as you noted, does have access to the map and has those capabilities).