I have to use a Windows simulation package to perform a repetitive task with slightly different options each time.
Since I hate repetitive clicking, on grounds of b
RIATest is not using Python but otherwise fits the bill. It is like Selenium but for Win32 and web.
RIATest uses Windows UI Automation API and can drive any Windows application that exposes its GUI to UI Automation properly (that includes all native and .NET apps).
Disclaimer: I work for Cogitek, the RIATest company.