This reflective writing discusses the challenges faced by aircraft designers in designing landing gears and the effectiveness of the proposed modifications to the landing gear of the CF188 to minimize the risk of planning Mechanism Assembly failure. The author evaluated static hold down force during the landing gear rigging, analyzed the impacts to the stability of the aircraft during landing and take-off, confirmed the increase of the bell crank gaps and the pin head, evaluated the aircraft ground handling at different ground speeds, and evaluated the loads on the planning and connecting links during many landings which include full stop, touch down and arresting cable engagement. The author proposed ways on how to design landing gear system with the minimum volume, minimum weight, reduced life cycle cost and high performance while observing the safety and regulatory requirements.