Joe,
If you're serious you should certainly look for a campaign manager immediately. It's already time or even past time to start planning your 2012 run for the mayor seat.
As far as getting volunteers working and asking for campaign donations, I wouldn't start bending the public's ear about all that money stuff until a year or less before the elections or you run the risk or boring them to death or making them suspicious of you.
But it's time to begin planning your campaign strategy right now.
You have to create your platform, create a plan for running your city or town, define how and why it's so much better than the plan of the person who will be running against you, study the budget and find out where there is too much spending or not enough spending. Talk to people and find out how they feel about local issues like property taxes, schools, police, fire & rescue, water and sewage services, plowing in the winter, street cleaning, garbage collection, crime, after-school progams (or lack), hospitals, neighborhood watches, leash laws, library policies, handicapped access policies, winter fuel assistance for the poor, 911 emergency response services, nepotism, corruption, petty or major bribery and scandals in local government, child protection services, school lunches, community evacuation plans for disasters due to storms, acts of terrorism or war, or other freak occurances.... all kinds of stuff.
Find out how all those things and more are currently being handled or planned for, find out how people feel about them and how they are being paid for, think about how you would do things the same or differently, write it all down, and brainstorm with your campaign manager and put it all into a platform that identifies you as the unique local Messiah who is the only leader who can get your city or town out of this ungodly mess your opponent has mired them down into.
And stuff like that.
You need to tell people why you would be any different than the current mayor, and not only different, but better. And now is the time to figure those things out. Money comes later, after you figure out if you actually are different and better.