A couple dollars pre day is nothing to most people but multiply by thousands of riders every day and it is a lot of money. There is no transit system in the world that couldn't be better with more funding so take that money.
You of course need a plan for the poor but that should be a minority.
I can't find the sources anymore but where I live, PT was never free, but there was no physical restriction to access it.
So by not paying your ticket/subscription, you only had to hope for not seeing controllers who could fine you.
A few years ago, they said that too many people were not actually paying for usage, so they decided to put physical restrictions (fare gates?).
Journalists decided to investigate and they did the math.
Basically they came up with something like : once you take everything into account (building and maintaining physical machines for buying fares and controlling access, managing everything around billing, enforcing fares with human controllers...), on every euro spent by a user, more than 60% went to the costs related to the fare system itself. Less than 40% was actual money that the company could use to improve the UX.
And obviously, the overall UX decreased because they also raised the fares.
So we're paying more, there's still lots of bad people in the stations/subway, but now we have to go through a metal gate to prove that we have paid the fare and do the same to exit PT.
Which, obviously, creates virtual congestion at peak hours, because the human flow is slowed and the width to pass is much narrower than it used to be.
Meanwhile, in another city, they went the other way : free PT.
I have yet to hear of some regular users seeing it as the decrease in UX.
You of course need a plan for the poor but that should be a minority.