Life in Toronto?

Happy to provide my thoughts as someone who has lived in Toronto for the majority of my life (but have only visited NYC on work trips and vacations - never lived there so take my comparisons with a grain of salt). Overall I think it is a great city with plenty to do, could definitely see it being similar to a smaller, cleaner, NYC as you mentioned. My thoughts on the topics you mentioned are:

Work Life / Salary: Obviously firm dependent, but have found that companies tend to be very collegial (but not too many work hard, play hard types). In general Canadians tend to be less direct than our American counterparts, which can mean firms seem more "polite" even when they are not. This is stylistic and can be frustrating to some. Salaries here are much lower than you would be used to in the US, but exceptions exist.  

Housing/Cost of Living: This is a hot topic at the moment as home prices have become very disconnected from incomes in Toronto. Still much lower than NYC but we earn significantly less as mentioned above. Coming from the US with USD savings should set you up well and things are still obtainable for those with a good finance job, but otherwise the math does not work out. A decent single family home in a good neighborhood (Little Italy, Davisville, Roncesvalles) would cost C$1.5-2.0 million. Cost would be significantly more in the very high income neighborhoods like Rosedale/Forest Hill, as you would expect. Rentals are more affordable with a nice 2 bedroom rental downtown being C$3k per month. Outside of housing, cost of living should be similar or slightly less than what you are used to in NYC.

Entertainment: The restaurant/bar scene here is fantastic, especially as you start to get to know the city outside of the main financial and entertainment district areas. There is also a ton of places to explore in the city (but it is harder as public transit sucks here). I am not a huge clubbing person, but I think there are a pretty good variety of decent options (I suspect the clubs here would not stack up to NYC though). Idk someone else is probably better positioned to speak to that. Sports teams receive a ton of support here, so great place to be if you are a hockey or basketball fan (not football though). Toronto struggles with good day/weekend trips. The wealthy here tend to have cottages in Muskoka and there are a few other big forest-type parks that can be nice to explore, as well as some small/cutesy rural options around, but most of the time you will be getting on a plane if you want to leave the city. Last thing to consider is that there is less "wow factor" to most of the entertainment around here just considering it is less of a tourist city compared to many US cities (even smaller ones) - if you like seeing A-list celebrities around town this is not the place for you.

This really turned into quite a long post so I hope this was helpful. I think the city is great (especially to balance having a family with the perks of big city living), but definitely need to keep your goals/tradeoffs in mind.