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Some quick googling, and it looks like it'd take 2-3 million to get the signatures, and another 20 million or so for advertising. It seems that someone like Poker Stars would be willing to pay this, if it meant the legislation would have favorable language for them.
There must be something I'm missing. Maybe they've done polls, and something like this wouldn't actually pass the vote.
It's very expensive, unfortunately. One needs to get the signatures, pass the signature verification, and then win any potential court challenges before and after the vote itself. And, of course, the vote itself would require a ton of PR to build voter support, as opponents won't hesitate to spend money to demonize the measure.
It it were easy, it would have happened already. Activists have tried this and getting volunteers to pitch in proved quite hard. You think it's hard getting people to send prefilled tweets? Try asking anyone to spend a day standing in the sun at the entrance of a mall with a clipboard while dodging security (because good luck getting permission for a "gambling" petition).