Sri Lanka now has a prime market for “vertical growth” and the private sector has become the main developer. However, the government has also contributed to these developments through the condominiums constructed for low income families. These were built for the purpose of re-settling people from shanties and recently, Tsunami victims. These condominiums have shown significant failures and problems. This paper looks at some of these problems; specially maintenance. Three types of condominiums were selected to study. Interviews were conducted with management corporations, selected occupants and professionals in the relevant authorities. The study focused on understanding maintainability problems related to technical facilities, management, social condition, and legal background. Twenty five technical management, social and legal related problems were observed that occur during the maintenance and operational stages. Some of them have become a huge burden to the government. Further, the study identified eight strategies from substantive experts to eliminate these issues now and in future attempts.