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I was just listening to the urbanist agenda podcast on this topic. It’s a good idea but not really easy to throw money at. You’d need to find a local group and work with them under the table.
The tax exempt political contributions seem like theyd be more effective. Even if ndp isn’t your party, you could probably convince more people to give that check up in protest if they are getting some back.
Also if we get somone good in power there will be less need for tactical urbanism. We can just have the more legal kind.