Historically disinvested communities have usable space for business and community development but the process of buying city-owned vacant lots and return the land to productive use is a daunting multi-year task. The IJ Clinic hosted a W(h)ine Night event where local entrepreneurs and community development leaders shared their experiences with vacant lot acquisition and how the process could be better. In the coming year, the Clinic will capitalize on this rich data to streamline and simplify vacant lot acquisition for ordinary Chicagoans.