Life-cycle assessment (LCA) and techno-economic analysis (TEA) were applied to assess the economic feasibility and environmental benefits of utilizing multiple biomass feedstocks for bioenergy products under three different technological pathways with consideration of uncertainties. Three cases were studied for the production of pellets, biomass-based electricity, and pyrolysis bio-oil. A Monte Carlo simulation was used to examine the uncertainties of fossil energy consumption, bioenergy conversion efficiency, stochastic production rate, etc. The cradle-to-gate LCA results showed that pellet production had the lowest greenhouse gas (GHG) emissions, water and fossil fuels consumption (8.29 kg CO2 eq (equivalent), 0.46 kg, and 105.42 MJ, respectively). The conversion process presented a greater environmental impact for all three bioenergy products. When producing 46,929 Mg of pellets, 223,380 MWh of electricity, and 78,000 barrels of pyrolysis oil, the net present values (NPV) indicated that only pellet and electricity production were profitable with NPVs of $1.20 million for pellets, and $5.59 million for biopower. Uncertainty analysis indicated that pellet production showed the highest uncertainty in GHG emission, and bio-oil production had the least uncertainty in GHG emission but had risks producing greater-than-normal amounts of GHG. Biopower production had the highest probability to be a profitable investment with 85.23%.