A work vehicle display system utilized in piloting a work vehicle includes a display device having a display screen, a context camera mounted to the work vehicle and positioned to capture a context camera feed of the work vehicle's exterior environment, and a controller architecture. The controller architecture is configured to: (i) receive the context camera feed from the context camera; (ii) generate a visually-manipulated context view utilizing the context camera feed; and (iii) output the visually-manipulated context view to the display device for presentation on the display screen. In the process of generating the visually-manipulated context view, the controller architecture applies a dynamic distortion-perspective (D/P) modification effect to the context camera feed, while gradually adjusting a parameter of the dynamic D/P modification effect in response to changes in operator viewing preferences or in response to changes in a current operating condition of the work vehicle.