As cost invested in developing the specified technology is increasing, investors are paying more attention to cost to benefit analysis (CBA). One of the basic elements of CBA for new technological development is the diffusion pattern of demand of such technology. Many studies of technology evaluation have adopted a single generation model to simulate the diffusion pattern of demand. This approach, however, considers the diffusion of the new technology itself, not taking into account a newer generation that can replace the one just invented. In this paper, we show how a multi-generation technology diffusion model can be applied for more accurate CBA for information technology. Monte Carlo simulation is performed to find influential factors on the CBA of a Cybernetic Building System.