The Smart Grid is not just about the digitalization of the Power Grid. In its more visionary acceptation, it is a model of energy management in which the users are engaged in producing energy as well as consuming it, while having information systems fully aware of the energy demand-response of the network and of dynamically varying prices. A natural question is then: to make the Smart Grid a reality will the Distribution Grid have to be updated? We assume a positive answer to the question and we consider the lower layers of Medium and Low Voltage to be the most affected by the change. In our previous work, we have analyzed samples of the Dutch Distribution Grid in our previous work and we have considered possible evolutions of these using synthetic topologies modeled after studies of complex systems in other technological domains in another previous work. In this paper, we take an extra important further step by defining a methodology for evolving any existing physical Power Grid to a good Smart Grid model thus laying the foundations for a decision support system for utilities and governmental organizations. In doing so, we consider several possible evolution strategies and apply then to the Dutch Distribution Grid. We show how more connectivity is beneficial in realizing more efficient and reliable networks. Our proposal is topological in nature, and enhanced with economic considerations of the costs of such evolutions in terms of cabling expenses and economic benefits of evolving the Grid.