The basic problem with the T is that it's a state agency. By which I mean, it depends on the support of the entire Massachusetts legislature, and if you are a legislator representing a district in western Mass, funding the T is a hard sell. Your constituents are going to be worried about crime, drugs, and unemployment, not a transit system that they'd have to drive for an hour to reach. The best you can do is make a general appeal to the Boston metro area as the entire economic engine of the Commonwealth, making its smooth running a win for all taxpayers in Massachusetts. Which, even though it's true, is not going to go over well with the public.
I've thought of one possible solution, which is to dissolve the T, blacklist and/or jail its top management as appropriate, and turn transit operations over to a new agency that's funded and run by only Boston-area communities who actually can point to a direct benefit from T service.
At least the T put the final nail in Charlie Baker's further political ambitions. Hopefully he'll stay at the NCAA, we're just going to have to ask college sports fans to take one for the team (pun intended) there.