I thought HN crowd might enjoy noodling this. I am a commercial real estate broker working with a large developer in a major North American city. This is the type of prisoner's dilemma I face.

Let's say we try to assembly a lot that consists of 10 properties with different owners (different sized lots). Developers can pay around x per buildable square foot, and that amount is higher for each individual owner than what they could get if they are selling their property individually. The fair way to pay everyone is to divide total amount the land is worth to the developer proportionally by lot size to each owner.

This is the problem that always arises: people get greedy. Not everyone, but at least 2 out of these 10 owner will be unreasonable. If everyone, or enough people get greedy, it kills the deal. On the other hand people who are greedy and hold out get more than people who are more amiable. So, from the stand point of the owner who wants to maximize their proceeds being greedy works, but only if everyone else is not.

I only get paid if the deal closes. If you were me how would you approach this prisoner's dilemma from my side?

Let's start with I have amount M that the land is worth, I have 10 owners with different sized lots. Now what? I have a goal to buy up the 10 lots at M or below. What should my strategy be here? I have to tie all the lots at the same time (I have 60 days from the day the first property is tied up, to buy the last one).

Thank you for your thoughts!