Urban heat islands significantly impact the health and well-being of the urban population. Urban vegetation can help regulate the urban climate by providing shade and evapotranspiration. This study examines the micro perspective of the urban climate and the heterogeneous urban vegetation's role in adjusting the microclimate with an innovative pipeline of workflow integrating Lidar point statistics, Machine Learning classification, and microclimate simulation with ENVI-met model. The method was tested in a comparative study on two sociodemographically distinct communities (Site A: Irvington, West, Site B: Centennial, East) in Portland, Oregon, USA, regarding their different urban tree structures and compositions and resulting differences in air temperature and other microclimate characteristics.