Will my town be mad at me if I appeal my assessment?
In short, no. Your local tax assessor is usually not as surly as you might think. Neither is your local board of assessment appeals. They are equally interested in insuring that you are paying a fair amount of taxes (a duty they are obliged to undertake) and that you are a happy resident and tax payer. In sshort, this is about making sure your assessment is accurate.
Another consideration is your neighbors. Maybe you think your neighbors will be mad if you end up reducing your appraised value. We find quite the opposite. We actually recommend getting together with your neighbors to help demonstrate the real fair market value of your properties if your assessments are too high. There is no point in paying high property taxes on a higher value that would not be reached on the real estate market.