>In Boston we constantly complain about the state of our public transit system
Have you seen the Big Dig? Look at the size of the check we wrote for that one. Now look at the kind of houses all the people who got to work on that project (whether in the office or in the field) in their mid and late careers (when you can make real money rather than be schlepping supplies around a job site for a "you haven't put in your time yet" size check) are living in.
Waste like that is why nobody wants to increase taxes. Pretty much anything more than the bare minimum seems to just slowly evaporate. The money goes poof before it trickles down into programs, infrastructure and services that actually provide benefit to the taxpayer. People would rather ride on a crappy T and pay marginally less tax than pay more tax to ride on a crappy T that has a handful more spots in the org chart for politicians to fill with people who won't show up.
Look at the semi-annual (well, let's be fair and give them credit, it's more like 3yr) state police "fraudulent overtime" scandal. It goes way, way back. Remember when the Probation Department got caught paying salaries to political appointees who didn't show up and didn't have any job duties? Remember when there was that enforcement/compliance arm of the Dept. of Elder Affairs that didn't actually exist like it was supposed to because the money was redirected to pay for more (politically appointed) middle managers who just forwarded emails all day? This is what "raising taxes" looks like in Massachusetts. For every $10 spent you'll be lucky to have a buck actually be used to run a bus, patch a pothole pay for healthcare, etc. etc. It's no surprise that people don't wanna pay for that.
People will pay for public services. Nobody really cares whether the garbage truck driver gets his pay stub on private letterhead or government letterhead. Nobody really cares whether they have public or private EMT services so long as they show up with equal promptness. What people won't pay for is public leeches and Massachusetts has done a very good job cultivating the perception that you can't buy one of the former without getting ten of the latter in the deal. No surprise that people don't wanna take that deal.