What a Fall Roof and Gutter Check Should Actually Cover
Most of what goes wrong on a roof in January was visible in October. This is the list we work through, and you can do a fair amount of it yourself.
Why autumn and not spring
Spring inspections tell you what winter did. Autumn inspections tell you what winter is going to do, which is the more useful information and the cheaper one to act on. Everything that fails between December and March in this market, ice dams, lifted shingles, blocked gutters, flashing leaks, is either visible or predictable in October. The work is also easier to schedule and cheaper to do before the first freeze, because a repair in November is a repair and a repair in January is an emergency call with a tarp on it.
One: the gutters, and the fascia behind them
Clear them. A gutter that goes into winter full of wet leaves freezes into a solid trough of ice, and that weight is what pulls hangers out of the fascia. While they are being cleared, the board behind them should be checked, because that is the failure you cannot see from the ground and the one that makes everything else worse. Check that every downspout actually discharges away from the foundation, and that the extensions are still attached rather than lying in the flowerbed where the mower left them.
Two: the valleys
Valleys carry more water than any other part of the roof and they collect debris where the two planes meet. Leaves and needles packed into a valley hold water against the metal and against the shingle edges, and in winter they become the point where ice forms first. Looking up a valley from a ladder at the eave tells you whether it is clear. If you have trees overhanging the roof, this is the single most useful thing on the list.
Three: flashing at walls, chimneys and skylights
Most roof leaks are flashing leaks. The places to look are where the roof meets a wall, around the chimney, and at every skylight. Rust streaks, lifted edges, tar smeared over a previous repair, or caulk doing a job that metal should be doing are all signals. Tar and caulk are the classic signs of a prior cheap fix, and they do not survive a freeze and thaw cycle. Chimney flashing in particular fails quietly and shows up as a stain on a bedroom ceiling in February.
Four: the shingles themselves
From the ground with binoculars you can see a surprising amount. Look for shingles that are cupping or curling at the edges, bald patches where the granules have washed off, any tab that is lifted or missing, and the ridge line for a sagging or uneven profile. Granules collecting in the gutter are normal in small quantities on a newer roof and a warning sign on an older one. A roof that is losing granules heavily is near the end and the useful question becomes planning rather than repair.
Five: the attic, which is the half people skip
Go up with a torch on a cold day. You are looking for daylight at the soffits, which tells you intake ventilation exists; insulation stuffed into the eaves, which tells you it does not; frost or staining on the underside of the deck, which means moist indoor air is condensing up there; and any bath or kitchen fan that vents into the attic rather than through the roof. That last one is remarkably common and no amount of roof work fixes it. This is also where ice dam problems are actually diagnosed, because ice dams are a heat escape problem rather than a roof problem.
Six: pipe boots and penetrations
The rubber collar around a plumbing vent is one of the shortest lived parts of a roof, typically cracking well before the shingles are finished. It is a small, cheap component and a failed one leaks straight into the ceiling below. Anything else that goes through the roof, a satellite mount, a dish, an exhaust, a solar attachment, gets the same look: is it flashed or is it sealed. Sealant is a maintenance item. Flashing is a repair.
Seven: overhanging branches
Autumn is when to cut them back, before the weight of wet snow brings them down onto the roof. Branches that touch shingles in wind abrade the granule surface, and a limb over the roof is both a debris source for the valleys and gutters and a risk in an ice storm. This is not roofing work but it belongs on the list because it is the cheapest preventative item on it.
Eight: the flat sections
Garage roofs, porch roofs and rear additions get forgotten because they are not visible from the street. Check for ponding that has not drained days after rain, blisters, open seams, and debris sitting against the parapet or wall transition. A flat section that ponds going into winter is a flat section that will hold a block of ice all season. Commercial buildings get the same walk, plus the drains and scuppers, which are the thing that actually decides whether a flat roof survives a Chicagoland winter.
What it costs to put right
Most autumn findings are repairs, and repairs in our market run $300 to $10,000 depending on scope and access. Gutter clearing and minor flashing work sit at the low end. If the check turns up a roof that is genuinely at end of life, residential replacements run $15,000 to $40,000, with larger or more complex homes at $40,000 to $70,000, and commercial or flat roof projects $25,000 to $75,000. The point of doing this in October is that you get to choose the timing rather than have January choose it for you.
Have someone look who will tell you it is fine
The useful contractor is the one who comes out, looks properly including the attic, and tells you there is nothing to do this year when that is the answer. We work across Cook, DuPage and Lake counties on residential and commercial property, and we quote roof, gutters and chimney separately so you can see each number. Free assessment, written scope, no pressure.