Wind power fluctuations impact power system flexibility and reliability, emphasizing situational awareness (SA) in wind power integration. Monitoring wind speed and power generation forms the core of SA, enabling insight into wind system conditions. An Integrated Development Environment (IDE) becomes pivotal in assessing the SA of wind-integrated systems, which is vital for forecasting operational reliability in power system planning. The IDE facilitates Simulink-based wind model development and is linked to dSPACE hardware through a real-time interface (RTI) for validation. This IDE-driven integration utilizes cloud-based Internet of Things (IoT) capabilities, acquiring wind speed and power generation data for precise SA evaluations. A multi-state wind speed model is employed to incorporate energy generation fluctuations. To improve this, the artificial neural network (ANN) model, i.e., a time series-based non-linear autoregressive with exogenous input (NARX) ANN, is utilized to predict future wind speed and power generation, strengthening SA-based operational reliability. The study investigates the effectiveness of a suggested operational planning strategy under wind generation uncertainties. This assessment is carried out within a real-time deployment of wind energy systems seamlessly integrated with IoT on the dSPACE platform. The primary objective is to evaluate the system's ability to maintain SA effectively.