The need for the better use of scarce planetary resources has never been more evident than it is today. However, this need is poorly reflected in human housing. In recent years, there has been a growing realization of the importance of constructing human shelters that better conserve energy and water through appropriate insulation and architectural designs. Among the important advancements in these areas is the use of rooftop greeneries for both energy and water conservation. This paper performs an investigation into this topic within the specific climatic context of tropical regions. Long-term experimental results are provided from a four-floor building in Kaohsiung in the southern part of Taiwan. The study involves a fully monitored extensive rooftop greenery and examines four different plant substrates, three different irrigation regimes, and different types of drought-enduring plants to find the most efficient combination of all three in providing maximum heat insulation and water usage efficiency. The attenuation of solar radiation through the vegetation layer is evaluated, as well as the thermal insulation performance of the rooftop greenery structure. Among the substrates, burned sludge has the best thermal reduction percentage of heat amplitude under the roof slab surface (up to 84.4%). Irrigation twice a week has the best thermal reduction percentage of heat amplitude (91.6%). Among the plant types, Sansevieria trifasciata cv. Laurentii Compacta and Rhoeo spathaceo cv. Compacta are found to be suitable for extensive rooftop greeneries because they have the best coverage ratio and are most drought enduring.