This report examines the problematic aspects of the regional development of two areas of the Southern Central Planning Region. The focus on the development of Haskovo and Kardzhali districts is an attempt to outline the need for joint efforts of regional communities for the purpose of integrated management of larger territories as well as the promotion of regional cooperation. In purely spatial terms, the two areas have one-size-fits-all problems, respectively the need for common solutions and the construction of sustainable regional infrastructure to improve the regional connectivity and competitiveness of their settlements. The focus of the report is to outline the strategic location of the two areas by grouping their specifics and outlining guidelines for improving the regional development of the two areas.