Population of Aspen was ~1200 at the time. Total vote was 377 people (173/204), or ~31.5% turn out. Someone with good charisma and a mini van would only need 7 car loads of 5 people to win this election.
In reality, if people want to take back the world, it doesn't take millions of dollars. It just takes some charisma a solid day of work and a minivan. Knock on doors, tell people you'll take them for free to a place with short lines. Check that they are prepared to vote, toss a cooler full of drinks and snacks in the back, and win.