Traditional situational analysis of a problem (conflict) is bound in its opportunities due to difficulties related with risk valuation and changing character of subjective probabilities of possible alternatives and reflection ranks of main actors. This paper focuses on the usage of multi role virtual games as a platform for the situational analysis. Particularly, it studies the opportunity to use Second Life virtual world as a universal base for modeling diverse complex, emergency and high-risk situations. The results of the "Hostage-rescue" test modeling experiment are discussed. Reconstruction of the real historical event "Operation Entebbe" (hostage-taking in a plane followed by a rescue mission, took place in 1976) and scenarios of emerging worst-case situation in a manned spacecraft are developed as a direction for further studies.