I'm starting a new, with more attention to detail this go round. I want it to be as real as possible, so I started at the transition between two cities (Lower Manhattan and New York City north of it), to make sure streets line up right. My last attempt was not up to standards, having problems at Canal Street, potential major problems in the future. Using the terrain (Pier 25 and Rockeffeller Park on the west and Corlears Hook Park on the east) to make sure I get it accurate as possible I found my street layout was going to start in the TriBeCa neighborhood.
The road going down to the southern tip is West Broadway, I did this to check my status. I traced the same street on my atlas and found it correlates to the true layout of Lower Manhattan. I did the same using Chambers and I believe this layout is on the right path. The streets are choppy, and ugly, but using a satellite view I made sure every block would give me a chance at decent realism and I'm staying possitive and having fun with this region.
Just working on the streets and a few buildings (schools, jails and landmarks) at this point. I decided to just build to get my region up in the millions. I few more pictures of the TriBeCa neighborhood and back to work.
At this point the grid is up to my standards, if you see any potential problems down the line, please let me know.