He seems like a meticulous fellow and as this is his last big baseball decision, he's not leaving any stone unturned
Toronto is not LA but it's also not Toronto from 1986. It's a pretty great place, especially if you're wealthy. Don't let Uncle Dennis make you think differently.
Also, Canadians tend to let the attitudes of American athletes temper their view of playing in Canada. Foreign athletes simply don't look at Canada the same way Americans do and we've already seen enough examples of American athletes choosing to be in Canada. Vince, Kyle, Demar all signed big contracts here. Halladay, Clemens, Canseco, Springer, Gausman, etc etc on the Jays side of things. The guy likely to end up the best player in Leaf franchise history is quite famously not from here, etc.
With international athletes I think it just comes down to basic shit. Money, weather (not a big issue for a baseball player at all), organization, travel, quality of the city compared to other league cities, etc.
I was watching some of Gil Arenas' podcast last week and they were talking about NBA media markets and they started ranking them. I expected his panel of all American former NBA players to completely overlook us, but Toronto came up immediately after the big markets (LA, NYC, Chicago) in the conversation and they considered it the 5th-6th biggest media market in the NBA to play in. Attitudes are changing.