Strange, in the example you uploaded, there is no loop back onto one of the steps after the responder. That is good.
Can you execute the CopyOfOrderHW1.vsm service in ITR mode.
When you send a request to the service, make sure the client is sending it to the IP address of the machine where you are executing in ITR mode. Perhaps, use SoapUI or Postman to send the request that way you can do it all locally.
If you single step through the VSM, when you get to the 'Booked' step and CLICK the next button, does the service go to the Responder step?
If you open the VSM with Notepad++, you will see an XML representation of your VSM.
Do a find on: <Node name="Booked"
A few attributes below that is an attribute that depicts the name of the step that will be executed when this step finishes (assuming it finishes successfully).
The Attribute should contain: next="Virtual HTTPS Listener 8105"
DevTest uses these Attributes at runtime.