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Municipal finance 101
Justin,
I will assume you are not a shill for Sam's campaign and that you actually care about why our transportation department needs an emergency bailout.
Transportation expenses generally fall into one of two categories, capital expenses and operating expenses.
For too long, the city of Portland has emphasized new capital expenses (building new assets), while underfunding the ongoing maintenance and improvement budgets for existing assets (both capital and operating expenses).
All those shiny new trolley, trains, and trams were built with the assistance of borrowed money which has to be repaid (with interest) to bondholders out of existing property tax revenues. That's a capital expense. Money spent on financing the shiny new trolleys, trains, and trams is money that is diverted from other transportation related budgets (like everything this new tax is being used for), and the costs of operating those new trolley, trains, and trams are subsidized (by the City, Tri-Met, and OHSU) WITH TAX DOLLARS.
Never mind the fact that rail consumes a disproportionately large percent of our capital spending (relative to the small number of taxpayers who use rail), and ignoring progressive's disdain for the automobile.
Why build new stuff when we can't afford to maintain the stuff we already have? Why pretend that the Federal Fairygodmother gives out "free money" to build new stuff, if they don't provide more free money to operate and maintain the new stuff?
Why should we trust Sam to maintain (let alone improve) gridlock on our roads and bridges when he has proven time and again that he views rails as the solution, and cars as the problem?
These are the kinds of question you have to answer in a democracy, especially when you're reaching for my wallet.