Approach

The approach to this exercise was to have a hypothesis to prove. Given the problem statement, preliminary logic would point towards check-ins and photograph posting being the most popular way of sharing information about interesting locations. If we take this assumption forward, we can try and analyse these two streams of data by contrasting them against geographic locations and see if they form clusters around specific areas.   
The first approach was to analyse the WPRDC dataset on Property Assessments in Allegheny County. At the onset, the dataset was far too big (418832 kB) to upload to Carto or indeed most other cartographic analytical software. However, after cleaning the data up, the bigger issue was realized as the geo-reference being Zipcodes instead of Latitude and Longitude and Geo-coding addresses while possible would cost.