This chapter explores the interplay between urban morphology, microclimate, and human-centric planning in high-density Hong Kong. Using Google street view (GSV)-derived 3D metrics—sky view factor (SVF), tree view factor (TVF), and building view factor (BVF)—the study quantifies street greenery, sky openness, and solar radiation to identify critical urban hotspots. Results reveal 12.6% of street points lack greenery (TVF = 0), concentrated in high-rise, narrow corridors, while 9.7% exhibit extremely low SVF (≤0.2), obstructed by dense infrastructure. Seasonal solar analysis highlights winter under-exposure in shaded W–E oriented streets and summer over-exposure in open coastal zones. Tailored solutions include vertical greening for cramped spaces, single-side tree planting for medium-width streets, and elevated bridge vegetation. This chapter validates urban canopy models with street-level data, assesses solar panel feasibility, and compares Hong Kong’s TVF (0.14) with Singapore’s higher greenery (TVF = 0.26). Case studies on Mong Kok’s themed streets demonstrate actionable strategies for integrating greenery and open spaces. By translating 3D morphological insights into planning practices, this work provides policymakers with evidence-based tools to enhance thermal comfort, public health, and sustainability in high-density urban environments.