We don't use this particular approach, but using Nginx and Passenger for Python applications has worked well for us for a number of years.
EDIT:
I seem to have missed that you're using Plesk for Windows not Linux, in this case my answer above won't help you. But perhaps something like this will: Deploy Django on IIS.
I am not at all surprised that this is a question. Python and IIS have seemingly been at war for years. I don't think that Python is on microsoft's list of first class citizens.