As someone who lived in New York for a long time (and calls myself a New Yorker but natives may take offense) but moved to Chicago recently, I find myself missing so many of the NYC amenities (subway/buses, entertainment, food, culture, etc) that Chicago has mirages of.

I can't see how Miami (also having spent a decent amount of time there), aside from the weather, could provide anything close to either NYC or Chicago. You have to squint even harder since Miami has none of the public transit, entertainment or other amenities I would expect from a large urban center. Plus, if you lean left on the political spectrum, you inherit the unpalatable politics that come with FL.

At least in Chicago I can buy a house within a ten minute walk to a beach and not break the bank. Something that, unless you're in Rockaway/LI or are ballin out on Star Island/Key Biscayne/Bal Harbor/etc wont get.

If you find people asking "why would anyone stay in NYC", they had no idea why they were there to begin with.