Objectives: Compared with Long-term Care 1.0 in Taiwan that emphasizes improving physical function with home-based rehabilitation, Long-term Care 2.0 adopts a home-based Reablement approach that emphasizes functional training. This study explores the practical obstacles when the providers implemented reablement and proposes corresponding strategies. Methods: Grounded Theory was adopted to qualitatively analyze the records of World Café meetings and advisory meetings collected from the Reablement Improvement Project in a southern city. Participants were the members of reablement teams who participated in the meetings (such as care managers, case managers, occupational therapists, physical therapists, and nurses). Results: 690 people participated. The practical difficulties of implementation included: (1) a limited understanding or misinterpretation of reablement and inadequate staff training to form a consensus on what reablement constitutes, and (2) difficulty in building an inter-disciplinary reablement network. The strategies to overcome these obstacles include (1) a client-centered and goal-centered approach, such as rapport building, individual goal-setting, and potential assessment and (2) exploration of a workable teamwork and communication mechanism, such as joint visits, joint staff training, and new communication platforms. Conclusions: Differing care values about aging and family and inadequate instructions and dissemination of the policy information contributed to the difficulties of implementing reablement. We proposed corresponding strategies for future research and policy making. Perspectives from policy makers and service users can be further explored.