Could a computer ever have a sense of what is a good space for humans to live in? Is there a calculation for how complex a maze is? Does it work for irregular shapes and three dimensions too? If so, it is probably a good starting point for figuring this problem out. Armed with that information plus a few more factors, we could start to build a computer program that locates desirable properties online and purchases them automatically if they are available.
As a "low-resolution" option, you could always replicate the houses in The Sims and see if artificial people like it.
Mokalus of Borg
PS - It might be best to keep the details of your approach from your investors, though.
PPS - I doubt many people would accept property decisions made with game simulations.