Availability of sustainable transportation fuels in future hinges on the use of lignocellulosic resources for production of biofuels. The process of biomass pyrolysis can be used to convert solid biomass resources into liquid fuels. In this study, laboratory experiments and process simulations were combined to gain insight into the technical performance of catalytic and thermal pyrolysis processes. Waste pinewood was used as a feedstock for the processes. The pyrolysis took place at 500 °C and employs three different catalysts, in the case of the catalytic processes. A process model was developed with Aspen Plus and a wide range of representative components of bio-oil were used to model the properties of the bio-oil blend. The results of the process model calculations show that catalytic pyrolysis process produces bio-oil of superior quality. Different technical process scenarios were explored based on the properties of the bio-oil after separation of water-soluble components, with the intention of producing a blendable or stand-alone product. It was found that—depending on the bio-oil requirements—sufficient hydrogen can be made available from the aqueous fraction to further treat the organic fraction to the desired extent. The resulting organic fractions are suitable candidates for blending with conventional fuels. The analysis results are used to provide guidance for catalyst development.