What kind of experience, capability and equipment does the dealer have? This will give you some idea of the skill level of the dealer. How many trucks does the dealer have? Are they in good condition? Both are related to how the company will be able to service your account.
Has the dealer already purchased the gallons they are committing to under the contract? How will they guarantee that the oil will be available? Some contracts will include language that says, "while supplies last." The contract should tell you what happens if the dealer is unable to provide you with oil because of oil supply shortage
Has the dealer offered contracts in the past? Make sure your dealer has experience offering contracts. You may also ask how their prices were last winter. Did they honor their fixed price contracts or have to increase the rate?
Will the dealer give you references from other customers? It is in the best interest of dealers to give you names and numbers of satisfied customers that are willing to speak with you. You can also speak with friends and neighbors who have experience with different companies. Local business groups may also be able to refer you to reputable dealers in your area.
Does the dealer have a customer service department? Do they offer round-the-clock service? Ask the dealer if they have a customer service number and the hours of operation. Ask what happens if you have an emergency during off-hours.
Is the dealer licensed? Oil heat dealers are not required to be licensed in Massachusetts.