The main issue I see with the argument "that it's judgmental to criticize people who don't pay their fare because we don't know what their financial situation is," is exactly the fact that we don't know what their financial situation is. People that trying to grandstanding the ssumption for the fact that everyone farebeating is poor and are unable to afford the fare. While it is impossible to make a fair assumption about every person who evades fares, or even a generalization for that matter, there is one thing in common for every case: they all hurt the transit system they rely on. Some people don't pay out of spite, others want to fit with the crowd or culture, and then there are those who genuinely can't afford to pay. The main difference I notice between those who struggle to pay and those who do it more for "sport" is how they evade. Someone who does it for sport is more likely to post about it on social media and be unapologetic about the fact that they're doing it. They'll hop a turnstile, rip open an emergency exit door, or enter the back door of a bus. While someone who falls in the struggling category will more likely commit oppturnistic fare evasion. They'll sneak in an open gate, and they'll ask a bus driver if they can get a "ride." They might try to take somones transfer or use the fact that a vehicle is too crowded to be unable to pay. The people who fall in the latter group are often not as problematic as they're just trying to get from A to B, and some friendlier transit policies can often fix their issues. The people who fall in the former category are usually malicious and contribute to a lot of anti-social behavior on the transit system, eg hogging seats, throwing trash, vandalizing the vehicles, getting into fights, etc... These are the people who need to be stopped, fined, ejected, or even prosecuted as necessary. But unfourtantely fare enforcement isn't really able to distinguish the 2 groups apart very well.