From Permits to Payoffs: Navigating City Departments as a Baltimore Investor

Real estate investor and Micasa Title partner Jacob Benzaquen joins Yaakov to break down the realities of investing in Baltimore. From surviving the 2008 housing crash and managing multifamily properties to tackling city bureaucracy, vendor hurdles, and regulatory red tape, Jacob shares hard-earned lessons on risk management, vendor relationships, and building lasting success.Whether you’re an out-of-state investor sizing up Baltimore or a local professional facing the city’s unique challenges, this episode offers practical strategies, candid insights, and long-term vision for navigating one of the most complex—but opportunity-filled—markets in real estate.