@bkcollecton
I don't know if it'll help you, but hopefully someone will find this helpful.
I just setup Static files for the first time following the guidance in that link I posted earlier. I used the Files tab in Dashboard to create a new root-level folder called 'public-html' and mapped it to a URL called /public/ using the Static files section on the Web tab of the Dashboard, then clicking the 'Reload' button on the Web tab. I ended up with:
URL Directory
/public/ /home/jgmdavies/public-html
in the Static files section of my Web tab.
So to do something similar to what you want, I could simply get my Python code to create the HTML files in my 'public-html' folder, and then they would be visible to the world via http://jgmdavies.pythonanywhere.com/public (you won't be able to access this, as I've got a password set).
This is independent of any Web apps, i.e. you could create the files using a Python app running in a Bash shell, or in a Scheduled job (or using a Web app).
HTH
Jim