Wamu
whats-a-matta-u?
It's tough, I have spent a lot of time in both cities. Toronto is the more complete city but Miami has the nightlife and the weather and lower taxes. But GA is an international player so he might feel the vibe of an even more multicultural city where raising a family long term would be a good idea. Will depend on what his priorities are. Maybe he just stays in Wisconsin.
Picking between Toronto and Miami is easy for me. Miami's located in Flordia. So I'm picking Toronto.