Too lazy to read everything, If someone already sugested this my appologies.
Start everyone together. Have the boat declare at the start of the Season A,B or C fleet. Overall award and Individual fleet awards.
As another "young manhattanite" I agree with your assessment of the NYC scene.
The Hudson and NY Harbor are not the ideal sailing conditions unless you enjoy current. 4 years sailing under a bridge at a "technical" school you get used to it. All I can see coming out of this new venture are...