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In the spirit of ‘Europe of the Regions’, local authorities are responsible for responding to the main interests, needs and preferences of the country’s citizens. Regional and local administrative authorities provide citizens with the necessary public goods, which reflect the trend towards ‘glocalisation’ in public administration at the European level, more significantly in the states in which the political system recently became democratic. With this background, the effectiveness of local self-government depends not only on local authorities’ decision-making freedom but also on (financial) support for it through decentralisation, and the member states of the European Union (EU) employ different strategies to achieve the same goal, with varying degrees of success. Within this context, our chapter offers a comparative analysis of the administrative, financial and local self-government decentralisation in member states, which include the southern and eastern regions on the outer edges of the EU. The general goal of our study is to identify the main trends in the present administrations and their challenges, as well as best practices that can offer lessons to other member states which are reforming their administration through decentralisation. In addition to the identified challenges, solutions and best practices, our study reveals a tendency towards consolidation at the level of regional government not only in the terms of legal responsibility but also of administrative budgets, thus generating an assumption of improvement in the general quality of governance in the member states.