We present an investigation of electrostatically-actuated carbon nanotube-based nanoelectromechanical switches. The primary goal of this study is to create a metric for design of robust, high-cycle devices. Methods for fabricating arrays of freestanding carbon nanotubes are discussed. Parametric studies, both experimental and computational, are then conducted to elucidate the failure mechanisms common to this class of carbon nanotube-based nanoelectromechanical systems, and to identify their point of onset within the design space. Experiments are performed in situ the scanning electron microscope, enabling direct imaging of device operation and the mode of eventual failure. Complimentary dynamic multiphysics finite element simulations of device operation are also presented to investigate the underlying mechanisms of the experimentally-observed failure modes.