The need for improving the productivity in freight transportation has become urgent in recent years due to rising fuel cost, labour shortage, healthcare cost for its labour force, and congestion on the roadways. This paper presents a productivity study about using three shorter, lighter trailers for moving household goods versus using one long, heavy trailer as commonly practised in the van-line industry. The conventional operations necessitate long delays due to loading and unloading. A goal of the proposed Shorter Trailer Combination Vehicles (STCV) operations is to maximise the operational efficiencies of long-haul trucks and the industry by dedicating such trucks to what they do best: moving, not waiting. A simulation approach is used to compare the performance of the conventional and STCV operations with respect to a stochastic Multi-Vehicle Pickup and Delivery Problem (MVPDP) in which the demand is random with random delivery due dates. The objective of the simulation is to determine the number of trucks and trailers, the pickup-and-delivery dispatch rule, and the type of transportation operations (conventional vs. STCV) that optimise various performance measures.