This paper presents a novel methodology for assessing islanding microgrids from the economical and functional perspective, for various stakeholders. The paper proposes the triggers for competitive deployment of microgeneration, storage, microgrid islanding, the market conditions that apply, and discusses the future tendencies and the policy recommendations to foster microgrid benefits. The validation of the proposed scheme is based on real market cases, where the triggers for autogeneration and islanding microgrids are present. Additionally, the new concept of grid independence cycle is presented and analyzed. The policy implications of a situation where grid consumption reduction leads to higher energy prices are presented and discussed. The paper concludes with a summary of prioritized technical and regulatory recommendations, proposed as a result of the assessment.