Applying a first-principles computational approach, we have systematically analyzed the effects of [2+2] cycloaddition oligomerization of fullerene C60 chains on their junction electronic and charge transport properties. For hypothetical infinite C60 chains, we first establish that the polymerization can in principle increase conductance by several orders of magnitude due to the strong orbital hybridizations and band formation. On the other hand, our simulations of the constant-height scanning tunneling microscope (STM) configuration shows that, in agreement with the recent experimental conclusion, the junction electronic structure and device characteristics are virtually unaffected by the C60 chain oligomerization. We further predict that the switching characteristics including even the ON/OFF-state assignment will sensitively depend on the substrate metal species due to the Fermi-level pinning at the substrate-side contact and the subsequent energy level bending toward the STM tip-side contact. We finally demonstrate that a force-feedbacked nanoelectromechanical approach in which both of the C60-electrode distances are kept at short distances before and after switching operations can achieve a metal-independent and significantly improved switching performance due to the Fermi-level pinning in both contacts and the large intrinsic conductance switching capacity of the C60 chain oligomerization.