Reminds me a little bit of how my dad used to try to get levies past for the school distrcit where he worked.  First you run the levy and publicize it heavily.  If that doesn't pass, you run it and allow no publicity at all.  Maybe those who voted against won't know to go to the polls.  Try it in the spring, but if that doesn't work, put the levy on a November ballot.  If the weather is terrible, fewer elderly people (who tend to vote against school levies) will be able to make it to the polls.  If you keep running the levy over and over again in different ways and with slight variations, it may only pass on a fluke or with a stroke of good luck, but eventually it'll pass.