Me: "How could I handle all these conditions? Would I be somehow able to implement them in the database so my code could just grab it there?"

Mentor: "No, that would be impossible"

Me: "Oh how about I just save them as a valid question in the db and the user will have to answer!"

Mentor: "No, you're supposed to automate that process for the user."

Guess I have to hard code it and can't rely on the good old humans.