Airports must maintain operational continuity while responding to changing demand and environmental conditions. This study assesses the operational readiness and resilience context of Djalaluddin Gorontalo Airport following infrastructure expansion by examining the interaction between exceptional aircraft demand, operational complexity, and historical weather exposure. A transportation system-of-systems perspective was applied using descriptive statistics, sample standard deviation, Z-score standardization, circular analysis of wind direction, and a Demand Amplification Ratio (DAR). The empirical assessment focused on 16 private/VIP aircraft movements during PENAS XVII 2026, comprising eight arrivals and eight departures, and historical weather conditions during June 2021–2025. The results show a DAR of 1.78, indicating that the recorded private/VIP aircraft activity was 1.78 times the routine scheduled-operation baseline used for the three-day comparison. The movements also extended across a longer operating period and involved diverse aircraft types, indicating increased operational complexity. Historical weather analysis showed that rainfall had the greatest variability, while relative humidity and wind speed were comparatively consistent, with no exceptionally anomalous June observation identified through Z-score analysis. The findings indicate that airport resilience should consider not only disruption and recovery but also the ability to adapt to exceptional operational demand under environmental variability. The study provides an evidence-based basis for strengthening operational readiness planning at regional airports.