The VLT at Paranal Observatory has been in operation for over two decades, and soon, the ELT will be managed by the same operational team. Maintaining operational efficiency and minimizing downtime with limited resources will be crucial. Previous research has shown that software logs effectively capture the telescopes' behavior, providing valuable operational insights. We've integrated various log analysis techniques from academic literature and industry best practices. These techniques allow engineers to monitor system health, analyze error sequences, detect anomalies, and reconstruct processes which improve maintenance and extract new insights. Additionally, we've utilized generative artificial intelligence and NLP transformer-based models, to infer observation behavior and predict execution failures. We have taken advantage of both the Paranal Datalab on-premise facility and Azure Cloud. In this work, we provide technical details and outline the key challenges and opportunities in adopting this technique within an astronomy facility.