Multiple Site Damage (MSD) is a typical problem of aging aircraft structures. On the other hand a similar situation may occur, if damages in the vicinity of the crack tip of a large crack is investigated. In some preceding papers the author has shown the possibility to assess the criticality of a MSD-scenario by comparing certain data compression measures of the crack scenario in an early stage. All of these scenarios were linked to cracks in one row of fasteners of equal distance, and the method was used in conjunction with the Monte-Carlo Simulation. The idea of using such ways to assess multiple crack scenarios is extended now in the paper presented here. The investigations are extended now in the sense that, the scenarios are more complex as they include large cracks and small cracks in the vicinity of the crack, where no fixed distance of the cracks is foreseen. The attempt is made to relate such results to experimental data on residual strength and therefore, to relate them to sophisticated models like the Gurson model.