Shallow slope failures occur almost every year during the rainy season. Continuous observation of the meteorological parameters and hydrological characteristics is required to more clearly understand the triggering mechanisms of shallow slope failure. In addition, influential factors, such as type of relative permeability models, air flow, and variation of hydraulic conductivity associated with stress–strain behavior of soil, have significant effects on the actual mechanism of rainfall infiltration. Real-time data including hourly rainfall and pore water pressure in response to rainfall was recorded by devices; then, the change in pore pressure from the devices was compared to the results from the infiltration analysis with applications of three relative permeability models, air flow, and the coupled hydro-mechanical analysis to examine an appropriate site-specific approach to a rainfall infiltration analysis. The infiltration and stability analyses based on the site-specific hydrologic characteristics were utilized to create maps of safety factors that depend on the cumulative rainfall. In regions vulnerable to landslides, rainfall forecast information and safety factor maps built by applying various rainfall scenarios can be useful in preparing countermeasures against disasters during the rainy season.