obtaining data associated with a vehicle service request, wherein the data associated with the vehicle service request is indicative of a pick-up location and a destination location associated with the vehicle service request;

determining, from among a plurality of candidate vehicles, a selected vehicle for the vehicle service request based on the data indicative of the vehicle service request, one or more candidate advertisement content items, and one or more candidate routes for one or more of the plurality of candidate vehicles by: analyzing the one or more candidate advertisement content items and the one or more candidate routes for the one or more of the plurality of candidate vehicles based on a determination of each respective candidate advertisement content item's ability to match with each respective candidate route;

generating a plurality of vehicle-route-ad sets, each respective vehicle-route-ad set comprising a candidate route, a candidate vehicle, and a candidate advertisement content item;

determining a value for each respective vehicle-route-ad set of the plurality of vehicle-route-ad sets based at least in part on at least one of an advertisement target area, an advertisement constraint area, or data indicative of one or more user preferences;

ranking each vehicle-route-ad set of the plurality of vehicle-route-ad sets;

selecting a highest ranked vehicle-route-ad set, wherein the highest ranked vehicle-route-ad set comprises a selected advertisement content item;

communicating data comprising executable instructions that, when executed by one or more processors of a display device, cause the display device to initiate display of the selected advertisement content item by a display device positioned on an exterior of the selected vehicle;

communicating data indicative of route information to a computing device associated with the selected vehicle, wherein the route information comprises a selected route to the pick-up location;

monitoring a current location of the selected vehicle obtaining location data from the location determining hardware of the selected vehicle and comparing the obtained location data to an expected location of the selected vehicle; and communicating data comprising executable instructions, that when executed by the one or more processors of the display device, cause the display device to update the display based on the current location of the selected vehicle.