Abstract: A system and method for many administrators to financially manage the parking of vehicles at parking locations where attendants record toll transactions with portable wireless devices, through a common, cloud-based central computer server. Each local transaction recording device, such as a hand-held PDA, stores the data for multiple toll transactions until confirming that a global communications connection meets a threshold level of quality, before transmitting the data batch-wise to the central server. In this way, data from hundreds if not thousands of toll transactions can be temporarily stored until reliably transmitted to the central server. The remote server is preferably under the control of a single service company that contracts with multiple parking management companies and operators to record transaction information and provide reports associated with an effectively unlimited number of parking lot locations and portals.