The biggest problem in New York City is parking.
...and paying for it. Monthly parking fees were higher than my rent in Florida.
And the main reason why I sold my car before I moved to Manhattan back in the day.
If you were lucky enough to find street parking - you then had to worry about opposite side of the street days when you had to move your car to the other side of the street for the street sweepers.
Between the cabs, Uber, buses and the subway - you really don't need a car in Manhattan, other than to leave the city on trips.
The other four boroughs (Brooklyn, Bronx, Queens and Staten Island) - cars are more likely to be a necessity.
And bringing us back on topic -
This is where this Cadillac program might have some traction.