Brattle Loop
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I think it's a great way to start getting our public transportation in this state to be free. Going by city each paying the cost for their residents is a very Massachusetts solution. Obviously if there was a greater Boston region governed on its own where the subway and buses operate within that area it could be done in one but that's not the case. Once some cities and towns start with giving their residents free T passes others will eventually jump on board out of jealousy and/or see how it helps with lessening traffic on roads and slowing the need for maintenance of the roads. We need to start somewhere to get ourselves to free Public Transit and this is the start or we can just argue about the outcome without giving solutions like us Massholes do.
Friendly neighborhood cynic here, come to dump cold water on yet more optimism but I think you're underestimating the byzantine - and frankly sometimes bizarre -mess that is local politics here. Anywhere outside the reach of the subway lines the calculus for municipally-subsidized fares is very different from within what is effectively fare zone 1A. That's a result of both the lower-quality service (CR frequencies < RT frequencies) and the CR's rapidly-escalating cost-over-distance fare zone structure. In the CR belt, you'd very likely be talking much higher costs per rider, for a significantly-smaller population that would benefit. That's not a formula that tends to be politically successful, something which does double in the gadfly-strewn NIMBY-mania that is some town politics. Boston, Cambridge, Somerville, maybe Brookline (though that's dicey) could probably have a critical mass of people in line to benefit (and people politically inclined to support it even if they don't personally benefit) but I question whether a good number of the other cities and towns in the district would go for it. That doesn't mean that the cities I mentioned shouldn't consider municipal subsidies for their own benefits, but the idea of it as a chain-reaction way of achieving the goal of no-fare-on-entry strikes me as highly unlikely to be successful.
As for the homeless they would just need to provide proof of residency like every other service from MassHealth to Food stamps to other local services that require it. An ID can be hard to get for the homeless but there are other ways to prove your residency. Heck that's another thing that should be free as it's needed so often State IDs.
This speaks to why a town-by-town solution is inherently less desirable than a radical policy shift at the state level. It's bureaucratic hoops to jump through that, even if you make it as easy as humanly possible, is still harder than being able to enter without trouble because there's no faregates. It would also fail to help boost use of the system by tourists (by definition not residents) and would be complicated for commuting workers and students, who you want to incentivize to not drive, but who would have to hope they were living in a town that chose to subsidize.
I'll reiterate my contention that while these proposals are not bad, they have significant drawbacks compared to doing it properly. It makes them worth consideration as interim steps if they have sufficient value on their own merits, but I don't agree that it's a way to bootstrap our way to a policy change on the statewide level, because I don't think it can reach the necessary critical mass.