Yay! I do belong in Portland! Of course I was super curious about Will's city so I made him take it too. He picked almost completely different answers and still ended up with Portland as well. At first he jumped up and celebrated. But then he was like, "That doesn't make any sense! I should live in Florida!"
Is it rigged? Probably. I'm sure there are only a handful of cities to choose from. But I'm going to take it as fate.