The article is devoted to the quantitative assessment of the economic efficiency of robotization in small and medium-sized industrial enterprises, taking into account the cost of capital and institutional implementation barriers, which is particularly relevant in the context of Industry 4.0 and the digital divide between SMEs and large corporations. The aim of the study is to identify threshold conditions under which investments in industrial robots and cobots generate positive economic added value for enterprises of various scales, as well as to assess the role of the institutional environment and the volatility of the cost of borrowed resources in shaping the “valley of death” of robotization for microbusinesses. The empirical base consists of depersonalized financial and managerial data from 485 enterprises across several industries that implemented automation projects in 2018–2023, supplemented by macroeconomic statistics and expert interviews with integrators and vendors of robotic systems. The methodology relies on modified NPV, IRR, PI, and DPP models that account for risk premiums and institutional frictions, WACC calculation with the allocation of a specific liquidity risk for SMEs, panel regression analysis of the relationship between the level of robotization and EBITDA margin dynamics, as well as scenario and simulation analysis using the Monte Carlo method to assess project resilience to demand and cost shocks. The results show that, given typical SME WACC values, the robotization of microenterprises often leads to a negative Mod. NPV and increasing financial risks, whereas medium-sized enterprises develop a sustainably positive investment profile with acceptable discounted payback periods; institutional barriers impose up to 30% of additional CAPEX burden and reduce IRR by double-digit values. The article discusses the phenomenon of the “efficiency scissors” caused by the transition from variable to fixed costs and provides recommendations for transitioning to RaaS service models, subsidizing interest rates, and developing cluster forms of robotization, which lower the entry threshold and make SME modernization economically rational.