The vertical motion configuration is a common design in triboelectric nanogenerators (TENGs) for energy harvesting; however, the performance optimization and comparison are still vague between various vertical motion-based structures. In this paper, time-averaged power density is defined as a metric to compare the power output performances of vertically structured TENGs, including contact mode and freestanding mode. To ensure comparisons under the same circumstances, a novel sandwich-structured dielectric layer was designed to maintain a stable and consistent surface charge density, with an extra rotating triboelectric nanogenerator working as a charge pump. We also investigated the impact of parasitic capacitance, which is a primary source of error in theoretical optimization. The freestanding TENG (FTENG) with a single dielectric layer demonstrates superior power performance, even when accounting for the influence of parasitic capacitance. This work provides valuable insights and guidelines for the design of high-performance mechanical energy harvesting devices.