Electrification, particularly in rural areas, is a significant concern for many countries as they strive to meet the Sustainable Development Goal (SDG) 7 of providing affordable, reliable, and sustainable energy. The current advancement of electrification is marked by gradual progress, primarily due to the significant expenses involved in extending the existing grid to the remote locations of rural communities to supply their comparatively lower energy demands. Microgrid technologies (MG) offer cheaper options to electrify remote locations and can promote economic growth (e.g. increased activities and energy demand) within the villages, especially as the MG transition to interconnected systems that offer a more reliable and affordable supply from the shared resources of multiple villages and grid-connected systems. This MG transition (i.e. from standalone-MG to multi-MG and grid-connected MG) should be planned in consideration of its link to village and energy demand growth. As extreme events have become more frequent over time, rural villages are vulnerable to weather events like windstorms compared with urban cities. Due to their isolated locations, repairing village support and energy systems can be time consuming. Therefore, inclusion for assessing the element of resilience in microgrid transitions should also account for their durability to withstand extreme events. This research work proposes a method for assessing the impact of extreme windstorms associated with high-impact low-probability (HILP) events on the MG network transitions while also considering energy demand growth. The proposed method is built on a Sequential Monte-Carlo Simulation (SMCS) framework and dedicated models to map the spatio-temporal evolution of windstorms that can impact MG. Furthermore, the proposed model also utilises a linear programming model to optimise the operation of MG as they transition and are impacted by windstorms. The model is demonstrated with applications to 28 standalone-MG located in the state of Sarawak, Malaysia. The results show that the MG transition naturally improves system resilience. Accordingly, due to demand growth, standalone-MG tends to experience increased impacts from extreme events. The outcomes of this research work aim to help policymakers and utility company to strengthen their electrification strategies, especially in rural areas.