1) Maintain good oral hygiene. 2) Have one go-to meal/dish. 3) Know how to use tools (hammer, screwdriver, wrench, etc.) and do a few minor tasks with them (hang pictures, put together furniture). 4) Handle yourself in a public speaking-type setting, like a job interview or giving a speech. 5) Make small talk/handle yourself in social situations. 6) Oh! And be able to handle your booze.

Do you have Flex Car or Zip Car in NYC? It might be worth it for you so you can grab a car when you want (and probably cheaper than renting).

Nothing as exciting as yours, but last week we took my 6-month old to Philly on travel and stayed in a hotel. I could tell he was keyed up being in a new place and knew he would never chill out enough for a nap unless I did something. So I walked him around the rooms (we got connecting rooms so he could sleep in peace) and described everything: "These are the beds," "This is the bathroom," "Those are the windows and outside you can see cars and buildings," etc. And he chilled out and was fine after that! I think he's a lot like your son - he likes to be told where we're going and what we're doing. And from the way he babbles constantly I think he's going to talk early and a LOT.