This essay addresses the question of how local elites maintain economic advantage during periods of political transformation. With the Chiang Family of Pei-p'u as its subject, this essay uses the family's account books to describe their economic behavior, including domestic finances and external investments during the Japanese occupation. In this process, the following issues are addressed: (1) the internal lineage structure of the Chiang family; (2) traditional land investment and Japanese-era property investment; (3) economic strategies of the Chiang family during this period of political transformation. While most of the Chiang family income came from traditional economic activities, most expenditures were for investments in Japanese property, with the result that the family came under a heavy economic burden. First, one important factor was that because adult males of the family died early of unnatural causes, the family lacked active economic planning. Second, during the time that major Japanese property owners and the Japanese monetary system were aggressively entering Taiwan's countryside, the Chiang family was unable to quickly shift its traditional land investments into market capital. That is, although already in contact with the world economic system, the Chiang family was unable to shift their income from traditional land holdings into investment capital to be placed in the emerging commodity markets. Third, the Chiang family had the demands on its domestic economy increased because of the higher land taxes introduced by the Japanese colonialists. Fourth, the Chiang family responded to changing realities through the traditional method of actively investing in the education of the next generation.