This paper experiments with some costs-benefit analyses, seeking a balance between soil-take and buildability due to land policy and management. The activities have been carried out inside the MITO lab (Lab for Multimedia Information for Territorial Objects) of the Polytechnic University of Bari. Reports have been produced about the Southern Italian Apulia Region, which is rich in farmland and coastline, often invaded by construction, with a severe loss of nature, a degradation of the soil, landscape, and ecosystem services. A methodological approach to the assessment of sustainability of urban expansion related, on one hand, to "plus values" deriving from the transformation of urban fringes and, on the other hand to the analysis of the transition of land-use, with the aim of "saving soil" against urban sprawl. The loss of natural and agricultural surfaces due to the expanding artificial lands is an unsustainable character of urban development, especially in the manner in which it was carried out in past decades. We try to assess how plus value can be considered "unearned", and to understand if the "land value recapture" can compensate for the negative environmental effects of urban expansion. We measured the transition from farmlands and natural habitat to urbanization with the support of the use of some Geographic Information Systems (GIS) tools, in favor of a new artificial land cover in the region of Apulia, Southern Italy. Data have been collected at the regional scale and at the local level, producing information about land use change and increases of property values due to improvements, referring to the 258 municipalities of the region. Looking at the results of our measurements, we started an interpretation of the driving forces that favor the plus values due to the transition of land-use. Compensation, easements, recapture of plus value, and improvement are, nowadays in Italy, discussed as major land-policy tools for managing environmental and landscape preservation. The interplay between urban economics and environmentally sound regulations reveals some controversial issues in urban governance and nature preservation: perhaps some abstract regulations, conjoined with non-case-oriented urban policies, consider these keywords as the old chemists considered the Philosopher's Stone. The analyses show criticality emerging themes in emblematic cases, studied in some municipal contexts.