Taiwan Businessmen’s Dongguan School (TBDS) is the first Taiwanese school to be recognized by both governments of the People’s Republic of China and Taiwan. After having experienced initial difficulties in establishing the school since its induction nine years ago, it has excelled and prospered beyond original expectations. In 2009, TBDS has grown to a k-12 comprehensive school with about 2000 students and teachers in the Dongguan city, China. TBDS not only is partly subsided by both Taiwanese business associations and Taiwan government, but also is provided some legal preferential treatments from China education authorities. Recently, the global recessions in the past two years also brought ruthless attacks on the financial condition and student attrition to these schools. TBDS has been slowly encountering more difficulties. The purpose of this study was to survey these related factors that influenced Taiwan businessmen in Pearl River Delta area (PRDA) when they chose a school for their children. Hence, the researcher conducted several focus groups, participant observations, and document analyses in order to better understand these related factors and provide some strategies to meet Taiwan businessmen’s various needs. Under the global economic recessions and the transitions of cross-strait, TBDS had felt the needs to respond flexibly. The research was conducted in two dimensions: 1) explored the social context in PRDA, 2) generated parental choice factors in neighboring cities. The results suggested four actions: 1) Government of Taiwan should try to assist Taiwan Businessmen in Pearl River Delta area for their children at subsidizing school fees and supporting to advance to a higher school; 2) open up for accepting students from closed regions; 3) enhance the sense of belongings among Taiwanese communities; and 4) be account for convincing the parents with regard to the benefits in Taiwan education system that TBDS had adopted.