I have had the fortune of taking several weekend trips to the Big Apple during the past year or so. However, all my trips were budget-oriented.
**Lodging--stay with friends! It makes for a cheaper, easier, and more fun trip experience.
**As for transportation, the subway system is extensive and easy to use, though crowded at rush hours. Walking is great too, in many neighborhoods of Manhattan it's the only way to go.
**Sightseeing in New York is as easy as any great European city. There is so much to see everywhere you go! I loved walking the back streets between Union Square and Washington Square Park. Times Square is a blast...I spent three hours cavorting with friends on the streets and in the restaurants. With energetic feet, you can wander for hours, window shopping expensive boutiques, grabbing fast food, or just people watching.