Not a list of generic tips. These are the questions whose answers actually change what you pay or what you are left holding, with the reason each one matters and what a worrying answer sounds like. Tick them off as you go — your progress is saved in this browser and never sent to us.
What the scope questions are about
Tear-offStripping the old covering to bare deck. Two layers roughly doubles the labour and the disposal tonnage.
Deck conditionNobody knows what is under the old roof until it is off. This is what an allowance and a per-sheet price protect you from.
UnderlaymentGoes down over the bare deck before the covering. Synthetic or felt is a line item worth naming in the contract.
VentilationA ridge vent runs the length of the peak under the cap shingles. Often quoted vaguely, and it affects how long the roof lasts.
Eave protectionA self-adhering membrane along the eaves, under everything else. In snow country it is what stops an ice dam pushing water back into the house.
Progress
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Before anything else: who are they
Everything downstream depends on this. Verify independently rather than accepting a number printed on a proposal.
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Scope: the lines that cause disputes
Almost every mid-job argument traces back to something that was never written down. Get each of these in the contract as a specific line, not a general assurance.
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Warranty: what is actually covered
There are two separate warranties and they fail in different ways. Manufacturer warranties cover the product; workmanship warranties cover the installation. Most leaks are installation.
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Money and schedule
Payment structure is one of the clearest signals about how a business is run.
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If this is an insurance claim
Claim-funded roofs follow different rules, and some common practices are illegal in some states.
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Common questions
How many quotes should I get for a roof replacement?+
Three is the usual advice and it holds up, provided all three are quoting the same written scope. Two quotes for different scopes tell you less than one detailed quote does.
Should I pay a deposit?+
A modest deposit is normal, and material deposits on special-order products are legitimate. Being asked for most or all of the money before work starts is not.
What is the single most useful question on this list?+
The decking one. Deck condition is unknown until tear-off, and a stated allowance plus a stated per-sheet price converts the most common source of mid-job disputes into a predictable number.
General information, not legal advice. Licensing, permitting and insurance rules differ by state and by municipality, and they change. Verify anything that matters with the authority having jurisdiction for your address.