In power systems with high shares of fluctuating renewable electricity production, flexibility options play an important role for system stability. Supplementary to existing technologies, new approaches for the provision of flexibility are under discussion. Among these, emphasis is put on decentral flexibilities at residential and commercial level that may become available by aggregation and market oriented coordination. Because future contributions of this concept to the coverage of flexibility demand will not only depend on technical solutions but also on viable business models, questions of economic incentives as well as regulatory issues are of particular relevance. Based on preliminary findings of an ongoing research project, this paper categorizes decentral flexibilities and presents key determinants for their utilization and merit. Considering current German regulatory framework and market conditions, major challenges along the aggregators’ value chain are discussed. It turns out that under today’s conditions the aggregation of (small) decentral flexibilities is a demanding business. On the one hand, it is difficult to reach an overall competitive cost level. On the other, misplaced incentives at the end customer level hamper the procurement of flexibilities from an aggregator’s perspective. Furthermore, revenue potentials on the sales side are limited due to a wholesale market situation that is characterized by overcapacities.