The i-DREAMS project developed a Safety Tolerance Zone (STZ) to define the point of safe self-regulated control, taking into account the significant impact of the human factor on safe driving behavior. This research aims to analyze the impact of critical factors like task complexity and coping capacity on risk. A naturalistic driving experiment was conducted in Greece, utilizing raw data from thousands of trips by representative drivers. Results showed that demographic characteristics, such as gender and age, correlated negatively with coping capacity, indicating lower levels in male and elderly drivers. Factors like vehicle age, fuel type, and trip difficulty increased task complexity. Coping capacity and task complexity were strongly correlated with driving risk. This paper will provide policy recommendations for implementing the i-DREAMS platform to improve road safety in these areas.