A computing system obtained input data including (i) schematic information associated with a load to be transported and (ii) requirement information associated with transport routes for each of multiple transport modes (i.e., railway and roadway transport modes). Artificial intelligence models determine dimensional parameters of the load based on the schematic information and define, from the dimensional parameters, a transport envelope of the load when carried on a transport for each of the first and second transport modes. For each mode, the models determine a metric that characterizes the transport envelope relative to the route requirement information and generate predictions regarding clearance of the requirements. A dual-mode constraint analysis compares transport modes using the predictions and generate a comparative recommendation, which is then output.