A representative sample was collected from an established two-year Hispanic-Serving Institution to explore the academic challenges currently enrolled Latino students are facing today and their perception of potential challenges when transferring to a four-year institution. A mix of exploratory data analysis and text mining analysis resulted in overall themes of financial barriers, academic preparedness and support, family culture and support, and the perception of the transfer process. In addition, through logistic regression analysis, factors that influence the decision to attend a four-year university will be explored with coursework requirements for transfer, family financial support, and distance from home and family being significant influences.