Housing projects come with problems of quality, quantity and the environment. These manifest in overcrowding, pressure on infrastructure, quality of construction, deterioration in environmental quality, uneven distribution of accommodation, unaffordable rents, high construction costs, nonavailability of housing finance, among other factors. This work seeks to examine the success or otherwise of the planning of the now implemented World Bank urban housing project in Owerri, Imo State and to suggest remedial measures that will help prevent the large housing estate from turning into a degeneration issue, as well as, suggest ways of avoiding planning errors for future similar projects. This work is based on the author’s participation during the pre-implementation planning and execution of the project. Flaws were identified in pre-investment planning, time scheduling, budget estimates, process manipulation and follow-up actions, and these gave rise to overruns and other failures. Recommendations were made on management of the estate, infrastructural improvement and completion, encouragement and enlightenment of the residents and putting in place a strategic plan for the future of the estate as some of the actions that should prevent degeneration.