I'm a gadfly -- I poke, I question, I wonder about flaws in the New Paltz political class. This is not a unique pastime, and plenty of people with a lot more smarts than yours truly have embraced the hobby. Some, myself included, have even run for office in the hopes that we could speak truth to power from within the power base itself. And that is where most local gadflies fall flat.
When you're a gadfly, by definition you focus on the negative. What's the point of questioning something if it works and everyone is happy with it? This is a dangerous mindset, because you only get noticed when you're complaining. People in New Paltz mock the gadfly that they disagree with, or call him rude or bombastic, or stop returning his calls. Some of us are well-qualified for the role because we're already rude and abrasive, but others have those traits thrust upon them.
Being a gadfly isn't a terrible basis for becoming a political candidate, but once you make the decision to run for office, New Paltz voters are pretty clear that they want you to switch gears. Complaining about the opposition is nothing new, because at least 75% of the politically engaged citizens are doing that already. Sure, a small sliver of people who hate your opponent will nod their heads and pull the lever on that basis alone, but New Paltz voters often want something more.
What they want is substance. What is your vision for the office? (Saying that you think having a "vision" for position X is a load of pretentious crap counts as a vision.) Do you have any thoughts on the problems facing the incumbent? (This is a popular question, but one I don't give much weight to, because armchair quarterbacks don't have enough information to make meaningful decisions.) What do you feel the big challenges ahead are? What attributes do you possess that will help you tackle these still-unknown issues?
Contrasting oneself to one's opponent is necessary, but it's part of a bigger package. You can't sell yourself as the "everything sucks guy" and expect to win the votes of more than a couple score of curmudgeons. Moreso than the country at large, people in this community are thoughtful and engaged. In 2011 two candidates got lackluster returns largely because they focused too much on what was wrong with their opponent and not enough on succinctly summarizing their own assets.
There are always going to be people that cast a vote based on gut, or personal relationships, or the malleability of the candidate. I'm not one of them; I've voted against friends and for people who are self-righteous jerks. My personal feelings about you have little to do with your ability to serve the community. My sense is that New Paltz has a lot higher percentage of folks who, like me, vote based on qualifications other than the ability to be a gadfly.