Feasibility of development projects and concepts often depends on the landscape ecological vulnerability. On the other side, landscape in many cases offers unacceptable space for new development trends. The system of landscape vulnerability and feasibility of development projects and concepts is based on the matrix composed of the landscape attributes (including nature and human dimension), and development activities. The rigid structure of these categories is softened by flexible set of criteria corresponding to the specificity of the situation. The assessment process consists of the analysis, expert examination and synthesis. The main purpose of the system is to establish an open and flexible expert support of planning and decision-making for sustainable landscape development.