Kingwaffles - great idea, great map. I don't care so much about the graphics, and I think it's too crowded for landmarks to go in there... Maybe just jazz up the colors a tad, like the San Francisco map.
Here are my suggestions (putting new territories in bold) :
1) Yes, add northern NJ territories - I'd suggest:
Weehawken above Hoboken
Secaucus (or Meadowlands) behind Weehawken
Teterboro above Meadowlands
up the river from Weehawken (in order),
West New York,
Edgewater, and
Fort Lee
Teaneck behind Fort Lee
Maybe even
Hackensack behind Teaneck and above Teterboro.
1a) Perhaps divide Harlem into Harlem &
Washington Heights?
1b) Perhaps divide Jamaicabay into JBay,
Far Rockaway, and Breezy Point
1c) Perhaps divide Ridgewood into Ridgewood &
Kew Gardens
2) Add in all of the bridges and tunnels:
Lincoln btwn Weehawken & Midtown
GWB btwn Fort Lee & Harlem
Whitestone/Throgs Nect btwn Unionport & Flushing
Cross-Bay Br connecting Jamaicabay and one of the Rockaways
Marine Pkwy Br, connecting East Flatbush & Breezy Point
3) Rename East Flatbush to Canarsie
Rename Dyker Hts to Bay Ridge
Rename Windsor Terrace either Gowanus, Park Slope, or Red Hook. Maybe make
Red Hook its own territory?
4) Make the three territories of Jamaicabay, Far Rockaway & Breezy Point their own region, with a minimal bonus.
5) Adjust all of the bonuses per the formula that someone posted earlier.
6) Orient the map up a little bit, so you have more blue water space to put the legend on the bottom.
I know that's way more than you were looking for, but opinions are free, and take them for what they're worth (nothing

). Hope it helps. Looks great so far!
Once I learn how to do maps, I am going to try to recreate the NYC Taxi map of Manhattan as a board.
Best,
Joe