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Cleveland Mayor Frank Jackson’s administration hopes to improve housing conditions by placing outreach workers with nonprofits across the city. The $1 million program would fund 14 “engagement specialist” positions with community development corporations, the nonprofit groups that help with neighborhood planning and other local work. The engagement specialists would send letters to property owners and work with homeowners and landlords to fix up housing in need of repair. Cleveland would spend another $500,000 to pay residents back for repainting home exteriors.