An analytical technique for investigating transport aircraft handling qualities is exercised in a study using models of two such vehicles, a Boeing 747 and Lockheed C-5A. Two flight conditions are employed for climb and directional tasks, and a third included for a flare task. The analysis technique is based upon a “structural model” of the human pilot developed by Hess. The associated analysis procedure has been discussed previously in the literature, but centered almost exclusively on the characteristics of high-performance fighter aircraft. The handling qualities rating level (HQRL) and pilot induced oscillation tendencies rating level (PIORL) are predicted for nominal configurations of the aircraft and for “damaged” configurations where actuator rate limits are introduced as nonlinearites. It is demonstrated that the analysis can accommodate nonlinear pilot/vehicle behavior and do so in the context of specific flight tasks, yielding estimates of handling qualities, pilot-induced oscillation tendencies and upper limits of task performance. A brief human-in-the-loop tracking study was performed to provide a limited validation of the pilot model employed.