First built in 2008 the city at that time contained a City Hall and a modernist skyscraper. Flanked by the Twin Towers it also had an elevated railway, working traffic lights and a cable car. The cable car was removed later that year and a monorail added along with the Chrysler Building Spire (thanks to Sean Kenney and Spencer Rezkella for their respective designs).
In 2011 the Twin Towers were removed and the city took on a more cluttered appearance. The monorail came back as did a subway.
By 2014 the towers were back along with some of the Lego official modular sets. In 2015 a few custom structures took centre stage.
In 2016 the city was at its largest. The Twin Towers were the focal point of the skyline but the real impact was the cluster of art deco inspired buildings (my own personal favourite being the blue). The city was divided into two districts; Downtown and Midtown. Downtown was home to the micro scale skyscrapers. Midtown - the official minifig scale sets.
This version of the city was taken apart in early 2017 and the project was shelved. In July 2017 the city underwent some rebuilding. The Twin Towers were replaced with a single modernist skyscraper and the city moved from mostly microscale to minifig. The blue art deco building was also increased in height and the Chrysler Building took centre stage. An elevated railway sat in the middle of the city, as it did in 2008 and there were plans to build more by the river.
By December 2018 the city had changed again. Whilst the skyline looked more impressive with the addition of the South Tower there were fewer buildings overall. All of the buildings by the river (along with the river itself) were removed. Plans for 2019 include rebuilding the river and a better road system along with more custom buildings.
I really like the realistic look of the river, and the elevated railway system. Those upside-down fences look like they were made for this. And that brick-built building (like, brick brick, not lego-brick. Ah you get the point ;-) )