The study deals with the sustainability of management in radiata pine (Pinus radiata D. Don.) plantations, focusing on management strategies that favor continuous forest cover and natural regeneration processes by balancing environmental and economic aspects. In a study area of Sardinia (Italy), tests were carried out in 45-year-old plantations through systematic and selective thinning, as well as regeneration felling. This was performed considering the current forest dynamism fostered by natural regeneration, and also the technical and economic aspects. Predictive models of work times, productivity, costs, and profit were built for the three observed treatments based on the experimental data. From an economic point of view, the various silvicultural management operations were always positive, with some differences depending on the type of intervention. The regeneration felling, with the planned natural regeneration of the pine forest in the following years, ensures the best economic results per unit of worked area, obtaining an average profit of about EUR 11,000 ha−1, as compared to EUR 9000 ha−1 of systematic thinning and to EUR 5000 ha−1 of selective thinning, along with other ecological benefits, including a continuous forest cover and the replacement of even aged plantations, increasing the biodiversity in forest stands (structure and species). The transformation of forest plantations into more resilient ecosystems on an economic sustainability basis can be effectively achieved through continuous coverage forest management approaches in the context of the study area.