Ultimately, I think it's impossible to tell if an Olympics is a good or bad thing. Every Olympics seems to be different and have a different effect on their city.
So true. I have been lucky enough to have been to a few Olympics over the years.
Athens suffered from the continuing barrage of "bad" news before the event. The media had no end of stories on how the facilities and infrastructure would not be ready, how the organization would be "Greek-style", by which it was meant chaotic, how terrorism would target the event, how security concerns would bring about gridlock in Athens, etc. As a result, many potential spectators stayed away and many tourists who would normally have gone to the Greek islands also avoided the country. Overall, Greece had fewer tourists that year than the previous year. No amount of advertising can overcome fears engendered by a global media campaign.
In the case of Montreal, one needs to remember when it took place. Expo and the Olympics took place within five years of each other - 1967 and 1972 - and anyone who lived in those years and those immediately before will remember it as a time when Canadians suffered a lack of identity and a sense of inferiority that would be unrecognizable today. The general belief was that Canada could not organize a world class event. There was an incredible swelling of pride when Canadians attended these events and realized we really could do something global in a way that was truly first class.
Another outcome of Montreal that benefitted Toronto was seeing how Canadians could drink and dine in outdoor cafes and enjoy themselves in public. Toronto was never the same afterwards. One forgets the Toronto blue laws of the 60s and while these major international events in Montreal did not alone change Toronto's strict morality codes, they were an important part of it.
Both Athens and Montreal showed the effect that Olympics could have when a country was ready to emerge on a world stage as an equal and serious player. Athens, although Greece is a member of the EU, is located in a pretty dodgy part of that region. Athens Olympics allowed the Greeks to show that Greeks are as capable at running a major event as any other European country. There was an incredible energy in Athens that summer as the Olympics came right after the Greek national team won the UEFA Cup. Canada also became a different country as a result of Expo and the Olympics.
The coming out to the world aspect of the Olympics was a major part of the Games in Tokyo, Korea, Australia, Mexico and no doubt a few others. In some cases the effect was sustained. In others, eg Mexico City, it was unfortunately not. This aspect is also a major driving force behind South Africa's hosting of the World Cup of soccer.
Right now Toronto has no credibility in organizing a major international sporting event.
Interesting also is the parsimony of Torontonians, and most of the rest of Canada - the habit of looking at everything strictly in terms of money expended. Whether it is a global event, human rights, refugee policy, public transport, etc., the number one issue of Canadian seems to be the financial costs. Since many benefits are future, social and/or unquantified, we are unwilling to look at much other than cost.
The other unfortunate tendency is the inability to see the world in any other terms than our own personal views. There is very little sense of larger community. So, if I am not interested in Olympic sports, it must mean that no one could or should be interested in them and we should not have them.