When it comes to existing buildings, the estimation of the structural residual bearing capacity is required to evaluate the potential for reuse/conversion. The level of detail and accuracy of surveys dramatically affect structural diagnostics. In order to optimise the experimental survey process, a simulation of the structural life-cycle may be useful. Based on a previously developed approach of Monte Carlo simulation implemented with a damage law for the life-cycle analysis of newly designed constructions, this paper presents the method application to a historic roof steel structure. It aims to identify critical situations, assess the residual life of the system, and plan possible retrofit strategies for the building conversion. The case s...