This paper discusses a systems approach to analyzing viability of resort-oriented regional development in devitalized areas, whereby our focus is placed on assessment of business administrability of small-sized industries supplying lodging services, whose demand is subjected to uncertainty in time. Two criteria are defined to assess the business administrability of lodging facilities from the long and the short perspectives. An assessment model of the business administrability is presented, which explicitly considers uncertainty of a profit stream. A case study in Wakasa Town, Tottori Prefecture, illustrates how this region can be vitalized, and demonstrates the applicability and potential of our model in assessing the illustrated points.