Except if I really wanted to be an awful human being, I'd just buy property, subdivide it, and then multiply my votes in the town election by the number of property units I've individually sold to my various LLCs.

This is kind of a violation of the "one man one vote" ideal that is the bedrock of our society. It easily turns in to "money buys influence" which is exactly the opposite of what made the US a great country to live in. If you don't understand that and you're a US Citizen you should really retake the civics / political science classes from high school.