Disclosed herein is a real estate management application with a “property check-in” feature that enables the agent to automatically check-in at each property location. Subsequent to entering a given property, the agent selects the check-in feature in a mobile real estate service application, allowing the real estate service to determine a present geographic location of the agent. Using this, the service identifies an MLS location of the client and uses corresponding MLS information to update a tracking entry associated with the agent. In embodiments, the tracking entry enables the real estate service to maintain accurate expertise history for each agent.