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[mashshare url="http://www.skyfiveproperties.com/blog/so-you-need-a-roofer-heres-what-to-know-before-signing-on-the-dotted-line"]So You Need a Roofer? Here’s What to Know Before Signing on the Dotted Line

Let’s be honest—new roofs aren’t exactly the most exciting home upgrade, but man, they’re important. Whether you’ve got shingles sailing off after a big wind or your ceiling just started a suspicious drip, finding the right roofer isn’t something you want to phone in. I’ve learned the hard way that a few extra questions upfront can save you a world of trouble (and possibly a soggy sofa) later on.
Start by Sizing Up the Roofer
The internet is brimming with ads for “great roofing deals,” but that doesn’t mean everyone with a ladder and logo is a pro. First tip: look for companies that actually specialize in residential roofing services. It sounds simple, but you don’t want someone who splits their time patching commercial warehouses or tiling patios—they probably won’t know all the little quirks (or city codes) your house needs.
Ask your neighbors, friends, or post in a local online group. Word of mouth is pure gold. If you spot a freshly roofed house a few doors down, there’s no shame in knocking and asking how it went!
Check Out the Paperwork—Yes, All of It
Here’s where I see people trip up most. Always ask to see proof of license and insurance. This isn’t being nitpicky—it’s just smart. A legit roofer will hand these over without blinking. If they hem and haw, or get dodgy, thank them for their time and keep looking. No one wants to end up on the hook for an accident because the crew had “forgotten” their paperwork in the truck.
You’ll also want a clear, written estimate. Get details in writing—materials, labor costs, the expected timeline, and what’s included if unexpected issues pop up (because, let’s face it, roofs love surprises). If you get multiple quotes, don’t just chase the lowest number. Sometimes you get what you pay for, and your “bargain” can end up costing more when corners are cut.
Communicate and Trust Your Gut
Good roofers talk you through the process, answer your questions, and keep you posted if the schedule shifts. If you feel brushed off, pressured, or patronized when you ask about ventilation or shingle brands, trust that feeling. My neighbor once hired a roofer who vanished for days mid-project, only to find he’d taken another job across town.
Ask about warranties, too. Most quality jobs come with both a manufacturer and a labor warranty. Get these on paper and keep them somewhere safe for a rainy day (literally).
Safety, Clean-Up, and Respect (It’s Not Too Much to Ask)
A good crew respects your property. Ask how they’ll protect your landscaping, where the dumpsters will go, and what daily clean-up looks like. I’ve seen nails left in driveways, flowerbeds squashed under ladders, and even a forgotten lunchbox in a gutter. The best roofers treat your house like it’s their own—full stop.
For more red flags to watch for—and smart ways to compare contractors—the Better Business Bureau has a fantastic hiring guide.
Final Thoughts Before You Sign
Don’t let the urgency of a leak rush you through hiring. Roofs are a big investment, and the right team makes all the difference between peace of mind and a season of headaches. Take your time, ask those questions, and remember—there’s no “dumb” question when it comes to the roof over your head.
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Kaya Wittenburg
Kaya Wittenburg is the Founder and CEO of Sky Five Properties. Since the age of 10, real estate has been deeply ingrained into his thoughts. With world-class negotiation and deal-making skills, he brings a highly impactful presence into every transaction that he touches.
He is here to help you use real estate as a vehicle to develop your own personal empire and feel deeply satisfied along the way. If you have an interest in buying, selling or renting property in South Florida, contact Kaya today.







