We consider a supply chain structure with shipments from an external warehouse directly to retailers and compare two enhancement options: costly transshipment among retailers after demand has been realized vs. cost-free allocation to the retailers from the development of a centralized depot. Stochastic programming models are developed for both the transshipment and allocation structures. We study the impact of cost parameters and demand coefficient of variation on both system structures. Our results show an increasing convex relationship between average costs and demand coefficient of variation, and furthermore that this increase is more pronounced for the allocation structure. We employ simulation and nonlinear search techniques to computationally compare the cost performance of allocation and transshipment structures under a wide range of system parameters such as demand uncertainty and correlation; lead times from the external warehouse to retailers, from warehouse to central depot, and from depot to retailers; and transshipment, holding, and penalty costs. The transshipment approach is found to outperform allocation for a broad range of parameter inputs including many situations for which transshipment is not an economically sound decision for a single period. The insights provided enable the manager to choose whether to invest in reducing lead times or demand uncertainty and assist in the selection of investments across identical and nonidentical retailers.