Reflection

Is there a middle ground between representation of data and accuracy? 

Yes, of course. especially if there are multiple objects near or on top of each other, as was the case here.  

How do you define the line between caricature and exaggeration? 

The size of these points of identification for features could easily overwhelm a map making it confusing it they were too big or too small. Additionally, color selection of overlays like neighborhoods could alter the appearance of the points. Lastly, order of the datasets, plays a pivotal role in clarity, placing the wrong dataset above another can mask it's intent.

  

To what extent should we caricature the data of city?

To the point of clarity, as mentioned above. It's a fine line to walk between clarity and confusion, we must stay cognizant of that as we gather data and develop maps.