This research identified the optimal scenarios to produce three bioenergy outputs: dual generation (electricity and heat), electricity, and heat in two regions located in the northern part of Costa Rica. Two biomass conversion technologies—boilers and gasification—with 2, 5, and 10 MW production capacities were assessed to ascertain the most suitable technology-capacity pairing for each bioproduct. To this end, a comprehensive financial model was developed to maximize the net present value. Following this, the equilibrium point for biomass supply and demand was ascertained, alongside estimations of the associated costs and energy utility. The findings indicated that the three bioenergy products could be completed within the local energy market at prices below 0.14 USD/kWh, with maximum supply distances of 90 km. The boiler and turbine technology proved most suitable for dual and electricity generation, with capacities ranging between 2 MW and 5 MW, where differentiation was influenced by biomass transportation. Furthermore, heat generation demonstrated financial viability at a capacity of 2 MW. In the evaluation of supply-demand break-even points, a maximum benefit of 26% was observed, with dual production yielding the highest benefits and heat production being the least favorable option due to the costs linked to biomass transportation and the low efficiency of energy transformation.