Any one know of any real life flight I can do in the New York region?
None AFAIK. Some private aircraft will do ISP-JFK and there are some ferry flights between LGA and JFK. I can imagine ferry flights between HPN/SWF to JFK and/or LGA but I’ve never seen one in person or in an app.
One time I saw a Delta 717 going from KLGA - KJFK
That’s one of those ferry flights I was talking about