Brattle Loop
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For it work, there would need to be a collective belief that the toll money would actually be used to make transportation systems better, directly or indirectly.
Okay, let's re-phrase my critique. You're correct that a collective belief that the toll money would actually be used to make transportation systems better is a necessary condition of and for implementing a scheme like this. What it isn't (and why that's not really a rebuttal as such) is a sufficient condition for it.
Believing that the money would go to good use doesn't change whether the transportation systems are sufficient to permit the tolls to be put in in the first place without a ridiculous backlash. It's been a few years, so my recollection may be off, but as I recall when the Patrick administration sought to raise the gas tax to raise transportation funds, that didn't get killed by concern that the money wouldn't be put to good (transportation) use, it got killed by objections to the tax increase.
You don't just need people to believe that the money will be put to good use, you need them to be willing to pay in the first place. That's a hard chicken-egg problem in this context, because you'd be asking a good chunk of people to take on direct extra costs for an indefinite period (until either transportation options improve or they reorder their entire lives) in exchange for the hope/promise of better future options. It's not an easy sell. In part because (especially if overly broadly implemented) there are plenty of people on whom the burden would fall disproportionately and/or on whom the benefits would be scant, if any. (Let's say someone works where there are jobs and lives where housing is cheaper, and has to commute via a road that will get tolled, but somewhere where the transit options aren't ever likely to be significantly improved absent, say, a megaproject of a radial transit line along the 128 corridor.)
Tolls can be regressive and unfairly burden low income people. With today's technology and electronic tolling, it would be easy enough to index tolls according to personal income. Tolls on every expressway inside 128, plus a few of the more major parkways (SFR, etc.), could (if allocated properly) provide funding for much needed transit improvements. Someone a few posts up stated that what we have now isn't working, and I don't see much Federal funding at all coming along for transit for decades to come. Tolling (indexed to personal income level) seems a sensible and fair way to raise revenue. It may also have the added bonus of decreasing traffic a bit.
I feel like this would be infeasible (and I personally don't think it would be advisable). I'm not a lawyer, but I strongly suspect that if a state tried to make income disclosure a condition of using its roads, the feds would drop an anvil on them. I don't think the states have any power to compel residents of other states to provide them with their tax returns or other financial disclosures, and there's no way the feds would permit a state to make doing so a condition of driving in the state. It'd be a legal quagmire. Not to mention it'd be a pretty serious privacy concern, in addition to being disastrously difficult to enforce. How would it even work? You couldn't base it on who owned the car, it'd take thirty seconds for someone to set up an ethically-questionable business of registering cars to people with sufficiently-low incomes. Meaning you'd have to have some way of knowing who's driving, meaning you'd presumably have to track them (and their movements) somehow, which would absolutely thrill people.