We study Supply and Demand Mediation type Transportation Service, which takes emotions of the service provider and the service user into account, mediates them, and dynamically changes transportation route and schedule. In this paper, we conduct simple simulations of existing and proposed transportation service, and show that the proposed service gives users shorter service usage time than existing services, however, we also confirm that driver's workloads of the proposed service increase. We remake and conduct a hands-on simulation of the proposed service, and clarify several operational problems of both the drivers and the users. The proposed service requires the driver to dynamically change routes in respond to the user requests, which are heavy burdens on the driver. In preparation for social implementations of the proposed service, we conduct an outdoor experiment on the campus of Yokohama National University. In this experiment, we implement two new routing methods and two reservation algorithms to reduce the driver's driving workloads and the user's troublesome operations, and interview the drivers, the users and, the operators at vehicle operation centers about their effectiveness. In conclusion, we verify that the new methods and algorithms resolve the problem of the proposed service.