Taking a quote apart, in order
Start with the paperwork, because it decides whether a quote is worth comparing at all. The first figure above sets the written-contract line, so a spoken quote for a larger job is not yet something to weigh. Ask for the scope, the price and the permits in writing, and check who will pull the permits. A quote that leaves any of these open is an incomplete basis for a decision.
Then look at the roof from the ground and from the attic, the two places a reader can check safely. Note how many layers are on it, if anyone knows. Look for any sag along the ridge or the truss lines, and for staining or gaps in the deck you can see. Write these down before the helper asks for them, because its next questions depend on them.
Only then compare the price. A published range is a sense check, not a bid. The helper's recommendation rests on the roof's condition and paperwork rather than on the total of a quote. A cheaper quote for a roof that nobody has yet inspected in writing is still a quote for a roof nobody has looked at.