The integration of artificial intelligence (AI) into drone operations has advanced the field, enhancing autonomy. However, evaluating critical aspects remains a challenge. This study proposes a combination of the “observe–orient–decide–act (OODA)” loop and the “analytic hierarchy process (AHP)” to evaluate AI-supported drone systems. The integrated approach assesses perception, decision-making, and adaptation. A comparative analysis of AHP results among different pilot groups, specifically experienced and less experienced pilots, reveals areas for improvement and guides technological development. The combined approach offers a comprehensive evaluation method for AI-supported drone operations, focusing on pilot group comparison. This research contributes to understanding the current and future state of AI-drone operations, informing advancements in the field.