An Ohio affordable-housing nonprofit that bought more than 1,800 apartments in the Chicago area has drawn the ire of its tenants and the city for the poor condition of its buildings. Now it faces a reckoning with investors that hold nearly $85 million in bonds on its properties.

Now, nearly two decades after the city’s public housing high-rises started coming down, one of the three strands in the transformative replacement plan continues to lag far behind the original vision. Sales of market-rate homes fizzled in the housing bust and a dozen years later have yet to catch fire again, other than on the old Cabrini-Green land.