Mom's roof is the kind of job where the number on the quote feels like the answer. It usually is not. The quote is a sketch of what someone plans to do. The signed contract is the promise. Your job is to make sure the two say the same thing before a crew shows up.
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Line up the work list against the quote
Pull every quote you have collected and put them side by side. For each one, find the line that says what actually gets done: tear off the old layer or lay over it, replace the flashing, replace the vent boots, haul away the debris. If one quote says 'roof replacement' and another says 'shingles,' they are not comparable. Ask each company to write its work list in the same terms so you can see the gaps.
Read the warranty as two separate promises
Most roofing work carries two kinds of warranty: one from the maker of the shingles and one from the company doing the labor. They cover different things and last different lengths of time. Ask who is responsible for each, how long each one lasts, and what you have to do to make a claim. Get the answers in writing. A verbal promise that the crew will come back is not a line you can point to later.
Write down the rule for added charges
Roof jobs grow once the old material is off. Rotten decking or damaged framing shows up, and the crew wants to fix it. Before you sign, ask the contractor to state in the contract how extra work gets approved. Does someone have to call you first? Do you have to sign a separate form? Is there a point where they stop and ask? If the paper says nothing, the default is whatever the crew decides on the roof that morning.
Check the paper before the crew starts
Confirm that the company name on the contract matches the company on the license and insurance papers you were shown. Make sure the contract states the start date, the finish date, a payment schedule tied to work completed, and who decides when the job is finished. Keep one folder with the quotes, the signed contract, the warranty papers, and any change forms. You will need that folder the first time a leak shows up.
If a term on any of this paper is unclear, the Sources page lists the public guides we rely on.