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I'd say NY has 7 months in the ideal range 60-85, whilst Miami has 5-6 months in that range. In regards to undesirable weather, I'd say that NYC has relatively mild winter weather compared to most of the NE/MW (only one month with avg. high below 40), and so it's both a shorter period of too cold, and it's not all that cold, compared to Miami's extended period of excessive heat/humidity.
I lived in both NYC and FL(not Miami but have spent time on and off in South FL).
They are both humid in the summer but will vote for Miami. Tropical, warm ocean water, green/lush year round, reefs/fishing, all those need nice weather. I remember I once swam at Jones Beach on LI in July and froze my ***.
I was in NYC this Summer and my experience was that the A/C was oftentimes underwhelming at best and often very deficient. Say what you want about the Miami heat and humidity (all true BTW) but one thing that you can't say about Miami and much of the South, is that the A/C doesn't work or it isn't persistent.
NYC is hotter than Miami in the summer, and colder than Miami in the winter.
Miami wins
Nonsense, NYC is about 5-7F cooler than Miami in the hottest month (NYC:84F vs Miami:91F), especially nights are much cooler in NYC. Of course, there are some extremely hot days in NYC, sometime it could reach 95+, but temperatures are usually in the low 80s or even 70s when it's cloudy. Miami is hot and humid for 6 months from May to October, and NYC only gets hot for 2 months (July & August).
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