Current aviation accident statistics indicates that the accident rate has become nearly constant at a level which, while being very low, is never the less unacceptable in terms of calendar frequency and it will increase with aircraft hours flown. Modeling and quantification of pilot errors is therefore a useful tool to gain a better understanding of what improvements in cockpit data presentation and activity might be necessary to achieve reductions in the world accident rate in predictable timescales. Hence, it is appropriate to investigate the piloting system using tools that have been proven to be successful in increasing the safety and reliability of the technical systems. This paper reports on work in progress that was aimed in the first instance at developing a methodology for modeling the piloting system by combining human factors with the mathematics of probability. It draws on a wide range of research and data from these domains, focusing them into systems methodologies using the Total System Intervention system that is widely demonstrated in industrial applications.