Detroit seems like a fantastic choice. Both Toronto and Chicago are fairly close. All the great Michigan and Ontario schools can be tapped and the city has tremendous potential to grow. Hopefully, they'd be nicer to their local population ala Facebook/East Palo Alto.
Speaking only for myself, "fairly close" is basically as far away as really far away. If I have to move, there's not much of a difference between moving 100 miles and 3,000 miles. If I were planning to operate in one city because it was fairly close to another city, I'd probably just go to the fairly close city instead (or somewhere else altogether).
