Abstract: Digital labor mobility is reshaping regional economies and challenging established models of migration and spatial development. This study examines how digital nomads transition into long-term digital settlers and what regional conditions support or inhibit that process. Drawing on Network Migration Theory and Lifestyle Migration Theory, a four-stage model of digital migration is developed based on duration of stay and regional embeddedness. The model is tested through an empirical case study of Greece using survey data, spatial analysis, and three-dimensional modeling. Findings indicate that while affordability and digital infrastructure are prioritized by short-term visitors, longer-term settlers consistently rank healthcare, municipal services, local safety, and geopolitical stability as critical conditions. Preferences shift systematically across the settlement continuum, with demographic factors such as gender and income further moderating settlement tolerances. The analysis, supported by 3D modeling reveals non-linear thresholds in perceived acceptability, especially for essential services. Importantly, digital settlement does not necessarily imply full-time relocation. Many digital settlers maintain a stable regional base while continuing to travel periodically and may eventually retire to these embedded locations. By linking digital migration to human capital dynamics, regional resilience, and spatial policy design, the study contributes to ongoing debates in economic geography and migration studies. Implications are discussed in relation to evolving EU and OECD frameworks for attracting mobile knowledge workers.