Self-organized monolayers of highly flexible Frechet dendrons were deposited on graphite surfaces by solution casting. Scanning tunneling microscopy (STM) reveals an unprecedented variety of patterns with up to seven stable hierarchical ordering motifs allowing us to use these molecules as a versatile model system. The essential molecular properties determined by molecular mechanics simulations are condensed to a coarse grained interaction-site model of various chain configurations. In a Monte Carlo approach with random starting configurations, the experimental pattern diversity can be reproduced in all facets of the local and global ordering. Based on an energy analysis of the Monte Carlo and molecular mechanics modeling, the thermodynamically most stable pattern is predicted and shown to coincide with the pattern which dominates the STM images after several hours or upon moderate heating.