We designed and developed a real simulator that can analyze the dynamic behavior of the machine operator-working machine-rough terrain system for a crawler crane, which is a typical crawler type working machine used on rough terrain. Using the simulator, we conducted an experimental analysis in which beginner level operators carried out load lifting, jib luffing and turning works while avoiding obstacles. Electroencephalograms, masseter voltage and line of eye sight were measured as the operator's biological characteristics. From the basic analysis of the measurement results, we examined the system that monitors the tipping safety condition of the machine during load handling work and transmits it to the operator through a visual and auditory system. Effects of the transmission pattern of the tipping safety condition to be monitored on the characteristics of the operation and related gaze (watching place and time) and also machine dynamic behavior were investigated. It was shown that transmitting the condition through the visual system when necessary and also adding transmission through the auditory system may contribute to ensuring tipping safety.