To improve the accuracy, efficiency, and ease of operations in the delivery process from pharmaceutical wholesalers’ sales offices to client facilities, the authors are developing an assistance system based on augmented reality (AR). This paper first outlines a prototyping cycle utilizing a virtual reality (VR) environment, which supports consensus building among multiple stakeholders and reduces rework in the development process. The cycle mainly consists of the design, redesign, and implementation of both AR-based assistance methods and the VR simulation environment, comparative evaluations of the methods, and information sharing with stakeholders. Next, the reproducibility of the implemented VR environment and the results of the comparative evaluation of different assistance methods are presented. Finally, we discuss the refinement of the AR-based assistance system, the estimation of its economic benefit, and the practical value of the VR-based prototyping cycle, based on exchanges with the actual development team.