Transportation infrastructure has formed the structure of Canadian cities over the past 150 years. This infrastructure has become expensive to maintain, and budgetary restrictions have brought the issue of fiscal sustainability to the forefront of our planning decisions. This paper will track the relative increase in transportation infrastructure funding against population and transportation infrastructure growth, to provide insight into the fiscal sustainability of existing transportation infrastructure funding models. Data from Waterloo, Ontario will be used to measure revenue sources for transportation projects over the past 25 years. Previous research aimed to identify the revenue sources that funded reserves and transfers in municipalities, but was limited by assumptions made about the contents of reserves based on the their current funding composition. By analyzing historical contributions to these reserves, a statistically accurate composition of these reserves can be predicted. The other component of this research will be a fiscal sustainability analysis, comparing quantitative metrics representing the physical size of transportation networks to the population of the studied region and the cost of maintaining those networks. This component will examine the extent to which new infrastructure is subsidized by the future population of a region.