The healthcare field has long been promised a number of exciting and powerful applications of Artificial Intelligence (AI) to improve the quality and delivery of health care services. AI techniques, such as machine learning (ML), have proven the ability to model enormous amounts of complex data and biological phenomena in ways only imaginable with human abilities alone. As such, medical professionals, data scientists, and Big Tech companies alike have all invested substantial time, effort, and funding into these technologies with hopes that AI systems will provide rigorous and systematic interpretations of large amounts of data that can be leveraged to augment clinical judgments in real time. However, despite not being newly introduced, AI-based medical devices have more than often been limited in their true clinical impact that was originally promised or that which is likely capable, such as during the current COVID-19 pandemic. There are several common pitfalls for these technologies that if not prospectively managed or adjusted in real-time, will continue to hinder their performance in high stakes environments outside of the lab in which they were created. To address these concerns, we outline and discuss many of the problems that future developers will likely face that contribute to these failures. Specifically, we examine the field under four lenses: approach, data, method and operation. If we continue to prospectively address and manage these concerns with reliable solutions and appropriate system processes in place, then we as a field may further optimize the clinical applicability and adoption of medical based AI technology moving forward.