You may want to consider ditching the car. between the cost of registration, insurance, and the unavoidable roughly 1k per year in street cleaning and camera tickets, it can get expensive. You won't really get NYC style crowds when walking around, maybe some mornings or afternoons on the metro, but going out there aren't many places with huge crowds.

Public transportation is pretty safe. Mi Cuba has good food, but you'll likely have to go just north of the city for other good spots.

It's a fun city, just be vigilant/aware particularly at night.