Over the last two decades, general aviation pilots in the US, especially those who fly light fixed-wing aircraft, have portrayed high rates of vulnerability to weather-related accidents. This high vulnerability rate is in stark contrast to the increased availability of weather forecasts, which has vastly improved given the wide variety of weather guidance now available online and in the cockpit. VFR into IMC flights is the leading cause of fatal weather-related accidents. A common contributor to these fatal accidents is the pilot’s inability to definitively assess the hazard prior to departure from the relevant weather guidance. Therefore, it is hypothesized in this research that the lack of sufficient weather reports and forecasts are not a core problem, but instead the primary contributing factor is an inaccurate or incomplete weather assessment by pilots before a flight. In this light, it has become apparent that pilots need a well-integrated route-based application that simplifies and organizes weather guidance in a way that requires less technical interpretation and gives time-based options to minimize a pilot’s exposure to adverse weather. Consequently, this presents the opportunity for a targeted software application that will eliminate or significantly reduce weather-related accident risk especially for pilots planning VFR flights.