The City of Portland has, for nearly 20 years, been managing stormwater bioretention facilities, known as green streets, in right of way locations. What started as a program with just a few facilities has burgeoned into an inventory of nearly 2500 publicly owned assets. Over the years, challenges and successes have helped shape how we view, manage, design and site these stormwater infrastructure tools. In a dynamic presentation format, we will discuss the evolution of condition assessment and facility asset management in Portland, Oregon and how that evolution has helped inform facility design and policy. We will dive into the specifics of how our lessons learned are informing policy changes for the City of Portland 2020 Stormwater Management Manual. Topics include site characteristics like urban heat islands, tree canopy, human impacts, sediment loading, soil challenges, climate and drought, as well as aspect, sun/shade, and upstream challenges and successes. Budget and cost as well as plant and tree selection and preservation, irrigation, weed management, safety and visibility will also be covered.