This is exactly why the human is in the loop and why the solution isn't purely software — to help come up with processes and mechanisms for resolving this sort

This is exactly why the human is in the loop and why the solution isn't purely software — to help come up with processes and mechanisms for resolving this sort of ambiguity. (Every outsourced bookkeeper today has this challenge, and there are a variety of options for resolving it, depending on what the customer requires.)