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The property tax system might not work. There are some areas in #Ontario that have 2 tier municipal government where public transit is the domain of the upper tier government. For example, York Region Transit is supposed to serve the entire York Region. Though in reality, there are several towns or sections of towns that don't get much in terms of service or have lost service.
If we have it paid through the property tax system, those who don't get service and must use a car, would end up subsidizing the more urban areas for their "free" transit rides. Public transit in North America is already subsidized, not sure if shifting the rest of the burden on to taxpayers would be fair especially if they can't benefit from the service at all.
It's going to be very hard to convince property owners would be willing to pay for something they cannot benefit at all to subsidize someone in the more urbanized section of the region transit access so they don't need to pay on the bus/train.