Renaturalization treatment in black pine afforestation is an important topic that should be considered. There is a need to favor the evolution of artificial pine forests toward natural forest systems. Overall, this study focused on pine forests, and suggests one typology of clear-cutting (dismantling cutting) on strips, which is associated with different extraction management techniques. Some ecological and environmental aspects associated with renaturalization treatments that have been applied by different mechanizations in black pine afforestation have been highlighted, as well as how renaturalization and the active ecological management of these stands could affect soil and vegetation. The main objectives of this research were to: (1) analyze the impact of silvicultural treatment and logging activities on forest soil, and (2) assess tree regeneration and floristic biodiversity in an ecological management system, in terms of both quantity and quality characteristics. These analyses were planned to obtain an overview of the environmental impact related to a multifunctional approach to the forest management of black pine afforestation. Essentially, the answers to the main research questions are: (1) less invasive extraction systems seem to use a cable yarder and forest winch; (2) a clear soil recovery trend with good capabilities is visible, in particular for the two extraction systems by cable; however, over a three-year period, only a partial but substantial recovery has been shown; (3) in general, silvicultural treatment showed qualitative and quantitative improvement in terms of tree regeneration; in particular, the extraction systems by forest winch and cable yarder showed better results; (4) silvicultural treatment seems not to have led to improvement at the level of the herbaceous and shrubby layers; however, clear differences are shown among the different harvesting systems. Significant recovery after use of the cable yarder was observed.