This paper thoroughly investigates the role of factors 'site' and 'situation' play on the regional development and the formation of the regional characteristics of Lo-Han-Boon area in Qing Dynasty period. Lo-Han-Boon was located at the hill area in the east of Taiwan-Fu (capital city of Taiwan during early Qing Dynasty). Mainly due to its disadvantageous natural environments, Lo-Han-Boon was one of the areas which were reclaimed by the Han Chinese in the later period in the southern Taiwan. Rugged badland terrain also provided a favorable place for anti-government people to hide in the early of Qing Dynasty from time to time. This caused a major threat to the safety of Taiwan-Fu, and Lo-Han-Boon soon became an area with strategic importance. The feature of this situation let the Taiwan officials did not dare to neglect the strategic value of this area. Hence, since1720's they set up border line with aborigines at this area, to assign officials to govern and servicemen to defend. This series of actions not only reserved a large living space for the aborigines at the north half part of Lo-Han-Boon, but also paved the base for cultural group distribution at this area till today. Besides, Lai-Boon was cultured to be the development center of this area, and became the most important center place at the hill area in the southern Taiwan during the middle period of Qing Dynasty. Along with the gradual development of Lo-Han-Boon area and illegal people fleeing further inland, Chi-Shan, however, has substituted for Lai-Boon as the major strategic site in the area. This shift also triggered the more prosperous development of Chi-Shan.