This Research to Practice Full Paper presents the experiences and lessons learned from five programs that provide financial awards and a holistic student support structure to low-income, academically talented students in Science, Technology, Engineering, and Mathematics (STEM). This report synthesizes the experiences of a diverse set of institutions, both public and private, that vary in size and geographic location. We have experience supporting students from a range of disciplines with an emphasis on students studying Computer Science. The goals of this work are to (1) outline the decisions that must be considered when designing a financial award program; (2) describe the interventions we have implemented and underline the institutional contexts that have led to their success; (3) describe the unique challenges posed by the COVID pandemic; and (4) highlight key elements necessary for successful program implementation. We specifically discuss the challenges we have encountered when implementing existing best practices. We report observations and results, some of which buttress those reported in the literature. Our work is intended to serve as a guide for educators who wish to implement programs to support students from financially disadvantaged and/or historically marginalized groups. By sharing our experiences and pain points, we hope to make it easier for them to design and implement effective programs adapted to their institutional needs and contexts.