The purpose of this dissertation is to guide economic policymaking by providing a comprehensive estimation of the effects that transportation revenue generation and infrastructure investment policies have on users. A 10-level integration framework is proposed to capture the complex research question of revenue generation-investment-benefits redistribution, via the use of activity-based modeling and innovative data integration techniques. Revenue policies are not evaluated based on their first-level impacts on payers alone. On the contrary, they are combined with transportation investment outlooks, and their performance is assessed based on how users eventually benefit from the revenues being invested in transportation projects that facilitate their travel experience. The revenue policies explored include the status quo (fuel tax), a fuel tax increase, a flat VMT fee, an income-based VMT fee, a transportation-dedicated property tax, and a transportation-dedicated sales tax. Subsequently, three alternative transportation investment outlooks are explored; these outlooks may be adopted by Maryland in the future, in an effort to redefine the state’s purpose, perspective and vision with respect to transportation. The selected outlooks capture some of the most popular and widely discussed future transportation vision directions for the U.S. transportation agencies, and include: (i) network-wide bottleneck removal projects funded by the state fuel tax increase of 2015 in Maryland, (ii) development of a bus-only network funded by a transportation-dedicated property tax that is invested locally, and (iii) infrastructure retrofitting projects to accommodate connected and autonomous vehicles, funded by an income-based VMT fee. The policies’ performance is evaluated on the basis of tax incidence, travel behavior and revenue generation metrics, while changes in welfare measures are estimated to assess the benefits redistribution due to the proposed revenue-investment dyads. The redistribution analysis shows that investing in bottleneck removal or CAVs will partially alleviate the burden that users will experience due to the fuel tax increase and variable VMT fee policies. However, in a situation where transportation funding shifts from the status quo to a transportation-dedicated property tax, lower income HHs will bear greater burden, and none of the income groups or counties will be able to recuperate part of their losses via the transit-oriented investment.