The disclosed computer-implemented method may include (i) receiving, by a dynamic transportation matching system, a request for transportation between initial waypoints, (ii) calculating, by the dynamic transportation matching system, a value metric for an initial driving route between the initial waypoints (iii) calculating a value metric for a walk-enabled driving route that comprises at least one alternate waypoint that is within a predetermined walking range of one of the initial waypoints, and (iv) improving, by the dynamic transportation matching system, a value of fulfilling the request for transportation by determining that a difference between the value metric of the walk-enabled driving route and the value metric of the initial driving route satisfies a walking-value threshold and selecting, based on the determination that the difference satisfies the walking-value threshold, the walk-enabled driving route for fulfilling the request for transportation. Various other methods, systems, and computer-readable media are also disclosed.