Entrepreneurship is widely celebrated as a core engine for economic innovation, personal autonomy, and social progress. However, existing academic literature often leans toward the unidirectional assumption that "entrepreneurship is inherently good," frequently overlooking the severe psychological, interpersonal, and organizational costs associated with entrepreneurial endeavors. Integrating Conservation of Resources (COR) theory, the Job Demands-Resources (JD-R) model, and multi-level entrepreneurial frameworks (encompassing individual, team, and organizational/societal levels), this study investigates the dual-sided nature of micro-catering entrepreneurship and its systemic adaptation mechanisms. Based on qualitative in-depth interviews and comparative case analyses of six micro-specialty restaurants in central Taiwan (five operational cases and one case transitioning from physical closure), this research reveals: (1) At the individual level, founders enjoy occupational autonomy and local attachment but suffer from extreme psychological strain, loneliness, over-investment, behavioral persistence/addiction, and constant operational anxiety; (2) At the team level, micro-catering ventures exhibit high human resource vulnerability, value misalignment, part-time staff integrity crises, and partnership fragility; (3) At the organizational and societal level, micro-catering generates positive social externalities through green dining practices (e.g., eco-chefs) and local ingredient sourcing, yet remains highly vulnerable to urban rent escalation, supply shocks, and platform commission pressure; and (4) Micro-catering ventures cross the "dark side" by constructing a tripartite resilience framework—comprising relational resilience (social trust density), operational resilience (micro-scale constraint design), and cognitive resilience (existential meaning-making). This study extends the theoretical boundaries of the dark side of entrepreneurship in service micro-enterprises and provides strategic guidelines for sustainable hospitality management.