Is it feasible to build a map using the google maps API or Openstreetmaps which has a superimposed layer that displays districts of a city? For example, Manhattan is a region within New York City, and I would like to be able to plot the boundaries of this region, and any neighboring regions on a map.

Where would one obtain the data for these regions (worldwide)?
I guess this can be achieved by using overpass turbo (which in turn uses the Overpass API) and the MapCSS styling feature by querying for all boundary=administrative relations with a certain admin_level=* tag (6 is for US counties). Although I'm not quite sure if the random colorization is actually possible.
Take this example as a start and see if you can improve it.
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