The development of shale oil often encounters a series of challenges, such as insufficient natural energy, rapid declines in production, and low oil recovery. Given its wide availability and low cost, natural gas serves as an ideal injection medium to enhance shale oil recovery. Based on the foundational data from Chang 7 block X in the Ordos Basin and considering the influence of reservoir stress sensitivity, this study uses numerical simulation methods in conjunction with the random forest algorithm to examine gas flooding in shale oil. This research aims to identify the key factors influencing the effectiveness of natural gas flooding for shale oil and to establish a chart for the adaptive natural gas flooding development boundary. The findings suggest that, for reservoirs with permeability less than 0.2 × 10−3 μm2 and oil saturation below 55%, it is advisable to adopt longer fracture lengths during hydraulic fracturing to achieve better development results. After 10 years of gas flooding, continuing the use of this method is not recommended, and adjusting of the development strategy becomes essential. For extended development periods, avoiding long-length fractures is crucial to mitigate gas channeling and ensure the effectiveness of the development process. This study offers theoretical guidance and technical support for developing shale reservoirs with natural gas flooding.