Due to the high initial costs and the uncertain returns of investment, the efficient green technology in shipping industry, shore power (SP), is still in a developmental dark age, especially its installation at bulk terminals and ships. This study examines the factors influencing the SP installation for bulk terminals and ships, elucidates the impacting mechanisms of one party's installation on the investment returns of the other, and reveals the decisive role of fleet operations in the installation decisions of both parties and corresponding carbon emissions. Employing a dataset representing real-world shipping routes and cargo types, the ship-cargo matching and ships' port-of-calls within a planning horizon are optimized with the objective of maximizing the profit of tramp shipping business by taking SP installation and usage cost into account. Portside SP decision-making model is also conducted to estimate the revenue generated by portside SP usage, and guide portside installation decisions based on the cost-benefit ratio. Finally, recommendations are proposed for ship owner, port operator and government to collaboratively navigate through the dark age of SP development, supported by the further discussion regarding fuel-electricity price gap and port loading efficiency.