Prostitute
Watch for the whores, they may seem to draw you in with their charms to make a quick coin, but in reality what they want is information. If you need dirt on anyone in the city, slip a prostitute a few coins and they'll indulge you in every last incriminating piece of information you'll ever need.
Prostitutes peddle their bodies on the street to make a living, but don't disregard them so quickly, as they know more about what is happening in their city than the best spy agencies.
Alcohol, sex, and a silver tongue can extract copious amounts of information without the suitor even being aware they have effectively been interrogated, making Prostitutes the ideal contact to keep on hand if you need to work under the radar. Thievery can also take place while their suitors are distracted, whether it's jewelry, money, or even their life.
Prostitutes tend to work together as a group, typically with one or two people acting as the business and management part of the job, while the rest work their bodies. The best brothels are invisible to the untrained eye, hidden in plain sight against the urban bustle, but know how to catch the best prey.