I like the idea of free transit for ticket holders. However, it shouldn't come at the city's expense. It should be funded similar to the UPass for post-secondary students.
I think the UPass is a brilliant solution. Charge everyone for a transit pass, whether they use it or not, and charge a lower price to each person than you did when you sold a student pass alone and bring in the same amount of money doing so.
For large-scale events at the Saddledome or McMahon or any other big venue, add a small $2 (or so) surcharge to every ticket sold and allow everyone to use their ticket as a transit pass for the day of the event. CT would bring in the same amount of money they do now and fare enforcement wouldn't need to be done (in 30+ years of riding the CTrain to Flames games, I don't think I've ever had my ticket checked after a game).
It also encourages transit usage, which benefits everyone, even if they chose to drive to the game. If you asked anyone sitting in traffic after a game if they'd be willing to pay $2 to get rid of 25% of the vehicles in front of them, you'd have a lot of people gladly handing over their toonies.
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