> What level of punishment should somebody who is trying to move between place to place receive for their lack of paying $1-3? The service was already going to operate, regardless of their lack of payment.
In Germany it's typically something like max(2 * regular fare price, 60 Euro).
I know you asked a 'should' question and this is an 'is' answer, but I hope it's still useful.
Google Translate on https://de.wikipedia.org/wiki/Bef%C3%B6rderungserschleichung... might be useful.
It's fascinating seeing your questions about something that's an everyday thing in all of the places I lived.
So in Germany it's typically the (public) companies running the transit systems that have teams that check that you've paid. Gates are almost unheard of for neither bus nor train. (I couldn't name one place in Germany that has gates for public transport at the top of my head.) The police would only get involved, if a passenger is getting violent or threatening to get violent, or won't get off the bus.
In Britain (and Singapore etc) you board the bus at the front, where the bus driver checks your ticket and otherwise will kick you off the bus. The bus driver itself won't get into a physical fight with you. But the bus driver can definitely call for backup and will (presumably) stop the bus and refuse to drive until a recalcitrant passenger has been dealt with. The social contract seems to that all the other passengers will blame the would-be fare evader for the stoppage and back up the driver. But I've never actually seen that acted out completely.
Trains in Singapore and many parts of Britain have gates, and there are usually either some people monitoring the gates for jumpers or at least cameras.
> Do you dedicate policing resources to ensuring the collection of what is certainly less than the cost to employ the police officer? Seems wasteful until you hit a very high ridership.
It's all pretty similar to how parking regulations are enforced: there's some dedicated people who write tickets (not police officers), and the tickets are typically a few dozen dollars.