
That doesn't look Kansas flat to me.
If you have less elevation/hills/moutains you'd need more distance (=plane further away), a lower difference in height between the two persons and/or a lower flying plane to achieve the same result.
Still, the concept would work if there is some elevation.
Of course, if the observer's height is > than the highest elevation, the plane would not ever disappear (except due to optical limits) unless the plane flies lower than the highest elevation.