Ask these seven questions and the sales pitch sorts itself out fast. We put this list together after years of meeting homeowners across Sumter County who had been burned by the crew before us, and every disaster story traces back to a question that never got asked. We answer all seven on every quote, in writing, and any roofer worth hiring will do the same without flinching.
One: are you licensed in Florida, and what is the number
Not “licensed and insured” as a slogan on a truck door; the actual state license number you can look up in two minutes on the DBPR website. Florida requires roofing contractors to be licensed, the lookup shows complaints and discipline, and a crew working under somebody else’s number or no number at all leaves you holding every liability the license exists to cover. While you are verifying, ask for the certificate of insurance too, sent directly from their insurer, covering both liability and workers’ compensation. If someone gets hurt on your roof and the workers’ comp is fiction, your homeowner’s policy becomes the target.
Two: who is actually on my roof
There is a world of difference between a company’s own crew and a subcontractor found on Thursday for a Friday job. Sub work is not automatically bad, but you deserve to know which one you are getting, who supervises them, and who answers for their workmanship in year six. Our answer is simple: our own crew, the same faces week to week, with the owner on the jobs. Whoever you hire, get the answer in writing, because the warranty conversation later depends entirely on it.
Three: is the price line-item or one mystery number
A single lump figure hides everything that matters: what shingle line, what underlayment, how many squares, what happens at the flashings, whether the old roof comes off or gets buried. A line-item quote lets you compare bids like-for-like and catch the corner-cutting before it is nailed down. It also protects the roofer, honestly; disagreements evaporate when the scope was written down. If a bidder resists itemizing, they are telling you the margin lives in the vagueness.
Four: who pulls the permit, and is it in my name
Every qualifying roof job in our counties needs a permit and a final inspection, and the permit should be pulled by the contractor under their license for work at your address. Crews that ask you to pull an owner permit are shifting the code responsibility onto you, and crews that skip permits entirely are leaving you with a roof that surfaces as a problem at sale time and at claim time. Permits are not bureaucracy; they are the paper trail that proves your roof was built to code by someone accountable for it.
Five: what does your labor warranty cover, in writing
The shingle manufacturer covers the product. The thing that actually fails on most roofs, workmanship, is only covered by the installer’s own labor warranty, and a verbal “we stand behind our work” is worth exactly nothing in year eight. Get the term, the coverage, and the exclusions on paper, and ask the sharper question: who honors it if the company is gone? Storm-chaser warranties evaporate when the truck crosses the state line. Ours is ten years, written, registered with the job file, and backed by a shop that has been at 70 County Road 532C in Bushnell through every season we have worked.
Six: what happens if you find bad decking
Tear-offs find surprises; that is the nature of tear-offs. The question is whether the surprise gets priced per sheet in writing before the job starts, or invented on your driveway at two in the afternoon with your roof open to the sky. We probe the deck from the attic during the quote, flag the likely areas, and put the per-sheet number in the contract, so the worst case is a known number instead of a hostage negotiation. Any bidder who cannot answer this question has answered it.
Seven: where is your shop
Not a P.O. box, not a phone number that forwards somewhere: a physical address you can drive past. Roof warranties are promises, and promises are only as durable as the company making them. Storm season fills our counties with out-of-town operators every year, and every winter we inherit their callbacks, their failed tarps and their orphaned warranties. A local shop means the company plans to exist here when your roof needs the promise kept.
Deposits, draws and when money should move
Florida has seen enough contractor deposit fraud that the law now says specific things about taking money and starting work, and the practical rule for you is simpler: money should follow milestones you can see. A modest scheduling deposit is normal; half the job up front before a shingle arrives is not. Materials on your driveway, tear-off complete, final inspection passed: those are the moments payment naturally belongs to. Be wary of anyone whose urgency is about the check clearing rather than the roof going on, and of prices that only exist if you sign today. Real numbers survive a week of thinking.
How to compare three bids without a spreadsheet
Line the quotes up on four things only: the exact shingle line and underlayment named, the flashing scope spelled out, the decking contingency priced per sheet, and the labor warranty term in writing. If a bid is vague on any of the four, ask once; if it stays vague, it is not the low bid, it is the incomplete one. The cheapest complete quote and the cheapest number on a page are rarely the same document, and the difference between them is where roof regrets come from.
Red flags that end the interview early
A few answers should simply end the conversation: no license number, insurance “in process,” a contract that assigns your insurance benefits, pressure to sign on the first visit, and any suggestion to skip the permit. None of those get better after the deposit clears. The seven questions exist precisely so these surface in your driveway instead of on your roof.
The bonus question: will you tell me not to buy
Here is the tell that finds the honest roofer fastest: ask what they would do if it were their house. A roofer who sometimes answers “repair it and wait three years” is a roofer whose replacement quotes you can trust, because the recommendation is not welded to the sale. A meaningful share of our free roof checks end with us telling the homeowner to spend nothing yet, and that is precisely why the eventual replacements come to us.
Why the list works better than reviews
Online ratings are worth reading, but they measure the jobs that went fine, and almost every roofing company’s reviews look similar until something goes wrong. The seven questions measure the opposite thing: what happens when the deck is rotten, when the storm season ends and the warranty call comes, when the price needs defending line by line. Those are the moments that separate roofers, and none of them show up in a star average. The list also has a useful side effect: asking the questions changes how the company treats you before the contract is ever signed. Crews that respect informed customers slow down, write things down and put their best people on the quote. Crews that rely on uninformed customers get visibly uncomfortable by question three, and that discomfort is free information delivered before any money moved. Fifteen minutes of asking beats months of wishing you had.
Put us through the list
Licensed and insured in Florida, our own crew with the owner on the jobs, line-item written quotes, permits pulled in your name, a 10-year labor warranty on paper, decking priced per sheet before work starts, and a shop in Bushnell you are welcome to drive past. Put us through all seven questions side by side with anyone else bidding your roof; that comparison is the whole reason the list exists. Call the owner at (352) 457-4472 or start with the free roof check, and see the finished work in the gallery.