I struggle with this all the time when trying to figure out how we get this polity to remove collective head from collective ass. Plenty of blame to Baker and DeLeo and so on, but they didn't fall out of the sky. This wild divergence between who uses the T and why and how it impacts their wallet is a part of it.
The polity has its head in its ass because the public does. I've seen a lot of people on FB today saying "I already spend X on the MBTA, and now I get to spend more. Thanks, MBTA!" People have no point of reference for what good transit costs. No one in the US provides it, and the MBTA has essentially never provided it. Absent that, all anyone can do is compare what they're paying for crappy service tomorrow to what they're paying for it today.
[Aside: Even if someone does provide it, transit is such a magnet for whining that the people using it never see it as good. This applies to London and Paris as much as DC or NY.]
Someone needs to do a study that folks will trust that suggests what good transit SHOULD cost, but there are a huge number of variables. Even if you know what the agency cost is, people can still pay in any number of ways (e.g., fares, sales tax, special taxing districts, parking fees, gas tax, surcharges on plane tickets, Federal Income Tax), all of which they tend to account separately. Places that have top-notch transit tend to either be privatized (e.g., Tokyo, Hong Kong) or have *ahem* other sources of revenue (e.g., Dubai and China).
There is a problem that low-income users feel fare increases with great severity. I believe the solution to this problem is to move away (as much as possible) from financing the MBTA through fare revenue. As it stands now, fare revenue is only a portion of the MBTA's funding. This portion is paid equally by riders of all incomes.
My ideal is inspired by the 1099-HC form that MA has tacked on to tax returns. Just have a checkbox form that people fill out with their taxes to acquire a monthly pass, where they fall into 3-5 income buckets. That form can have a Rider ID code on it for each MA resident that's tied to your payment account. The Commonwealth knows how much I make each year - it's just a matter of bringing that information into the process properly.
RI and NH could add the form as well, or there could be an online system for non-residents with some other form of verification. People already have to provide proof-of-income to receive discounts - why should the burden only fall on them?