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I think you would lose a lot of money. Bikes and skateboards alone are going to have tons of violations. Also, I feel like if i had to bet money, boats aren't going to be included unless specified in most but crucially not all circumstances.

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If it's even odds then I expect it's a losing bet no matter what anyone writes down - that's why in the imagined scenario it's forced. The pertinent question isn't whether you expect to lose money by playing, it's whether you expect to lose less money by including non-motorised vehicles in your write-up than by excluding them.

Personally my instinct is that I'd lose more money by specifying skateboards and bikes as I've usually seen those addressed by their own signs rather than being included under "vehicle".

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