IMO one should think about the bond disconnections theoretically, and figure out a couple pathways that may work. Furthermore, assignment of the forward synthetic pathway with reagents and FGI's is when a plan can become infeasible with certain or all FGI's. The more FGI's in one step the better the synthesis is (e.g. manipulation of alkenes by oxidative cleavage can install multiple functional groups in 1 step...), or the less number of columns (practically).