This paper is an addendum to a recent publication on a Comparative Study of 3D Wing Drag Minimization by Different Optimization Techniques; with a focus on a path forward towards the development of a larger-scale Aerodynamic Optimization Workshop. Three independent optimization efforts were conducted concurrently, each without knowledge of the others' results. The resulting "optimal" wings were then cross analyzed by each of the CFD methods used in the optimization phase, and by a fourth CFD method which was not used to develop any of the geometries. The incremental improvements, as predicted by these cross analyses, are compared to establish a level of uncertainty in the performance improvements and identify any unusual trends. The baseline geometry of this pilot project is the DPW-W1 wing, which was placed into the public domain by the Drag Prediction Workshop as a test case for the third workshop of June 2006. Lessons learned from this collaborative effort are documented and suggestions are provided to aid in the preparation of a possible future workshop on aerodynamic shape optimization.