A written scope before anything else
Any estimate worth trusting should name the actual work being done, not just a total price. That means the underlayment type, whether a full tear-off is included, what happens to the old decking if it needs replacing, and what the ventilation plan is. A verbal estimate that skips straight to a number is asking you to trust a memory rather than a document you can compare against another quote line by line.
If a contractor is reluctant to put the scope in writing, that reluctance is worth paying attention to before it becomes your problem partway through the job.
Inspection before pricing
A proper roof estimate starts with someone actually walking the roof, not estimating from photos or a drive-by. That inspection should include a look at the attic where access allows, since that is where ventilation problems and hidden water damage show up before they are visible from the shingle side. A price given without an inspection is a guess, and guesses tend to change once the crew is actually on the roof.
Ask what the inspection covers and whether photos will be part of what you receive. A contractor who documents findings has less reason to surprise you later.
Crew size and how the job actually runs
A larger crew, ten to fifteen or more, finishes a standard residential roof faster and reduces the number of days your house sits with an open deck, weather permitting. Ask how many people will actually be on the roof and whether the same crew handles the whole job from tear-off through cleanup, or whether different stages get handed to different subcontractors with less coordination between them.
One point of contact from the estimate through the final sweep matters more than most homeowners expect until they have dealt with a job where nobody seemed to be in charge.
How storm and insurance work is handled
If the job involves an insurance claim, ask whether the contractor documents damage in a format built for an adjuster and whether they will meet the adjuster on site. A contractor experienced with storm claims in this climate should be able to explain the process clearly without pushing you toward a full replacement before an inspection has even happened.
Be cautious of anyone who promises a specific settlement amount before an adjuster has seen the roof. That is not something a contractor controls, and a straight answer will say so.
Clean-up and what happens at the end
Daily clean-up and a magnet sweep for nails and screws at the end of a job are small things that matter a great deal in practice, since a driveway or yard left with debris is the last impression a job leaves regardless of how well the roof itself was installed. Ask what the end-of-job clean-up actually includes before you sign anything, not after the crew has already left.