While I agree with the general sentiment and wouldn't like to see street cars go, keep in mind that the Toronto's subway system is very underdeveloped compared to world-class cities like London, Paris, New York, etc. Toronto is one of the few major worldwide cities that don’t have subway/train...
I don't think Toronto will surpass New York or even Chicago any time soon. I've been to both NYC and Chicago several times, and they are huge cosmopolitan cities with fine architecture and it's evident that there's a lot of money there. It looks like Chicago is more affordable than Toronto...
I've lived in several major cities across Europe and North America and Toronto is at the top of my list. The only thing I don't like is the really long winter, but this winter we have had it really easy so far :)