We used to play games with the Long Island railroad conductors back in the 70s. A crew of about 10 guys from my neighborhood had season Ranger tickets and would take the LIRR home after the games. From Penn Station, we only went to the first stop, Woodside.
We would wait on the platform until just before the doors closed so we could scope out where the conductors were entering the train. Then we would board keeping as far away from the conductors as possible. Usually there were too many passengers for the conductor to get to us by the time the doors opened at our stop.
Then they got wise. They were ready to ambush us!
Once The train started moving, four conductors got out of their seats, put on their hats and started punching tickets and collecting fares in our car.
That trip they got us!
The next week It happened again, but we were ready for them.
As the conductors got up and put on their hats, the $100 bills came out! Being unable to count out the appropriate change quickly, the fare was less than $3 IIRC, many of us escaped once the doors opened.
The ambush conductors, who we later learned were just dead heading home to the Island, gave up. There were no hard feelings.
The Woodside Crew had prevailed!!!
Sometimes on a very crowded train, the conductor will just never get to me before my stop. Or I think sometimes they give up in frustration when they can't even get down the aisle through all the people standing up.
That's why I won't activate my e-ticket until the conductor is upon me. They always say on loudspeakers at the stations to activate your tickets before boarding the train but only the rookies actually do that. I purchase 10 and 20-trips so try to make them last as long as possible.
Another trick was to head to the lavatory when the conductor entered your car. Then when he passed by, leave and move to car he was just in. I never tried that one but heard about it.
I don't think these tricks are as easy these days as they have "eyes in the sky" in every car. I'm sure those can be viewed in real time by the train staff.
Also, I'm sure they train conductors to change their routines each trip to catch people like your Woodside Crew!