Detailed structural building information is used to estimate potential damage from hazard events like cyclones, floods, and landslides, making them critical for urban resilience planning and disaster risk reduction. However, such information is often unavailable in many small island developing states (SIDS) in climate-vulnerable regions like the Caribbean. To address this data gap, we present an AI-driven workflow to automatically infer rooftop attributes from high-resolution satellite imagery, with Saint Vincent and the Grenadines as our case study. Here, we compare the utility of geospatial foundation models combined with shallow classifiers against fine-tuned deep learning models for rooftop classification. Furthermore, we assess the impact of incorporating additional training data from neighboring SIDS to improve model performance. Our best models achieve F1 scores of 0.88 and 0.83 for roof pitch and roof material classification, respectively. Combined with local capacity building, our work aims to provide SIDS with novel capabilities to harness AI and Earth Observation (EO) data to enable more efficient, evidence-based urban governance.