I think you can ask the same question about any fair division question, and I really don't know how to answer that. Perhaps is the answer is that we are optimizing for how fair our morality says the division is.
our morality
If you are asking humanity, give the money to charity.
If I was one of the two people involved, I'd suggest using the 20 dollars to buy us both dinner (or other jointly enjoyed purchase...charity still works). The social trick leaves neither indebted to the other - in fact it can strengthen the bond.
You can't come up with a general solution to division problems, because human morality doesn't work that way. We've got really idiosyncratic notions of fairness, especially in cultures which have property rights.
In "Principles of Disagreement," Eliezer Yudkowsky shared the following anecdote:
I have left off the ending to give everyone a chance to think about this problem for themselves. How would you have split the twenty?
In general, EY and NB disagree about who deserves the twenty. EY believes that EY deserves it with probability p, while NB believes that EY deserves it with probability q. They decide to give EY a fraction of the twenty equal to f(p,q). What should the function f be?
In our example, p=1/5 and q=17/20
Please think about this problem a little before reading on, so that we do not miss out on any original solutions that you might have come up with.
I can think of 4 ways to solve this problem. I am attributing answers to the person who first proposed that dollar amount, but my reasoning might not reflect their reasoning.
I am very curious about this question, so if you have any opinions, please comment. I have some opinions on this problem, but to avoid biasing anyone, I will save them for the comments. I am actually more interested in the following question. I believe that the two will have the same answer, but if anyone disagrees, let me know.
I have two hypotheses, A and B. I assign probability p to A and probability q to B. I later find out that A and B are equivalent. I then update to assign the probability g(p,q) to both hypotheses. What should the function g be?