Abstract: A system for managing a plurality of properties includes a letter server, a client device, and a plurality of provider devices. The letter server is operative to store a plurality of letters for delivery to the plurality of properties. The client device is operative to electronically communicate with the letter server so as to generate the letters, and to generate a plurality of delivery orders each of which identifies at least one letter of the plurality for delivery to at least one property of the plurality. The provider devices are each operative to electronically communicate with the client device so as to receive delivery orders, and further operative to electronically communicate with the letter server so as to receive the at least one letter identified by each of the at least some delivery orders. Each letter of the plurality conforms to one or more of a plurality of regulatory requirements.