Since it is all relative, from the observer on the ground it is all the velocities added together since they are all moving in the same direction. The car at the bottom is moving at 49 MPH, a person standing on the trendmill relative to the car at the bottom moves forward at 50MPH resulting in a speed of 99MPH to the stationary observer. A car travelling on top of a stationary treadmill would result in the car travelling in 100MPH, since the treadmill itself is travelling at 49MPH, that is added, so the final speed is 149 MPH.
Assumptions made are that the treadmill and cars have enough power to maintain it's velocity as additional load is placed upon them. Any resulting acceleration is "instant" or the treadmill is of sufficient length to accelerate the top car to it's final velocity. These assumptions are made as there is insufficient information to make more detailed calculations.
An interesting note 149MPH/129.5 Knots is about the top speed of a C172R in level flight meaning the plane could land on the car without changing it's speed. Also if it landed on the treadmill, the plane's speed would not change.