Diversification of smallholder rice-based cropping systems has the potential to increase cropping system intensity and boost food security. However, impacts on resource use efficiencies (e.g., nutrients, energy, and labor) remain poorly understood, highlighting the need to quantify synergies and trade-offs among different sustainability indicators under on-farm conditions. In southern coastal Bangladesh, aman season rice is characterized by low inputs and low productivity. We evaluated the farm-level impacts of cropping system intensification (adding irrigated boro season rice) and diversification (adding chili, groundnut, mungbean, or lathyrus) on seven performance indicators (rice equivalent yield, energy efficiency, partial nitrogen productivity, partial potassium productivity, partial greenhouse gas footprint, benefit-cost ratio, and hired labor energy productivity) based on a comprehensive survey of 501 households. Indicators were combined into a multi-criteria performance index, and their scope for improvement was calculated by comparing an individual farmer’s performance to top-performing farmers (highest 20%). Results indicate that the baseline system (single-crop aman season rice) was the least productive, while double cropped systems increased rice equivalent yield 72–217%. Despite gains in productivity, higher cropping intensity reduced resource use efficiencies due to higher inputs of fertilizer and energy, which also increased production costs, particularly for boro season rice. However, trade-offs were smaller for diversified systems including legumes, largely owing to lower N fertilizer inputs. Aman season rice had the highest multi-criteria performance index, followed by systems with mungbean and lathyrus, indicating the latter are promising options to boost food production and profitability without compromising sustainability. Large gaps between individual and top-performing farmers existed for each indicator, suggesting significant scope for improvement. By targeting indicators contributing most to the multi-criteria performance index (partial nitrogen productivity, energy efficiency, hired labor energy productivity), results suggest further sustainability gains can be achieved through future field research studies focused on optimizing management within diversified systems.