A portable, automated contractual image dealer and transmitter provides a platform capable of managing, manipulating, storing, and transmitting digital media files across a wide array of transmission means and protocols. In addition, the capability to provide media for sale or distribution from remote locations, including the ability to choose from a number of possible buyers based on selected criteria and to remotely establish binding purchasing and/or image transferal relationships, is potentially beneficial for an array of media applications. In one embodiment, the transmitter may be employed by photographers, photojournalists, and/or the like to rapidly process, edit, and send photographs or video to multiple news agencies, newspapers, magazines, television studios, websites, and/or the like while maintaining control over their photographs by allowing them to send reduced quality and watermarked proofs. The transmitter may be configured to allow users to first generate and transmit low-resolution preview images.