After further testing the point where the mount failed last time, the teeth constantly skip to the point where its no longer lifting the weight, rather constantly skipping. Although the FlexSpline seems to have a lot of strain on it, the motor itself doesn't. While the teeth are skipping the motor is running at about 0.230 Amps. This is a very small amount, meaning its using a very small portion of its power. This is due the Planetary Gear acting as a multiplier on the Strain Wave Gear.

I am now going to take a step back in ratio in attempt to make the teeth of the FlexSpline Larger. Ideally this will stop the skipping from happening. Since there is little strain on the motor I am not worried on the lower gear ratio in the end. I may be looking into a 20:1 Strain Wave Gear which would leave the Gearbox with a 100:1 Ratio. With that Ratio the final design could still output close to 100NM of torque if everything goes to plan.