01
The attic, first
Almost everything worth knowing is visible from underneath, and almost nobody looks. Daylight at the deck edges. Staining on rafters and trusses, and which direction it runs. Rusted nail points, which mean condensation rather than a leak. Insulation that is matted or dark where air has been moving through it. Prior repairs nobody mentioned. A roofer who has priced your roof without going in the attic has priced an assumption.
02
The ground, slowly
A full lap of the house before anyone puts up a ladder. Roof planes read against each other for sag or a line that is no longer straight. Fascia and soffit condition, which report on years of runoff and on whether the intake ventilation is even open. Gutters checked for accumulated granules — a roof that is shedding its surface tells you so down here first.
03
Penetrations and transitions
Then the roof itself, starting where roofs actually leak. Pipe boots, whose collars perish in this sun long before the surrounding roof is finished. Vents and curbs. Valleys. Wall terminations and step flashing, where the failure is usually that somebody relied on sealant instead of building a lap. Skylights and chimneys. And every place a slope ties into a low-slope section — a lanai, a porch, an addition — which in Florida is the most reliably problematic detail on a house.
04
The field, and the fastening
Only now the open surface. On shingle: granule loss, cupping, brittleness underfoot, whether the sealant strips ever bonded, and fastener placement — overdriven, underdriven, or high above the nail line. On tile: cracked and slipped pieces, foot-traffic damage, the state of the ridge and hip work, and the age of the underlayment beneath, because on a tile roof the tile is the wear surface and the underlayment is the roof. On metal: seams, panel movement, and exposed fastener gaskets, which are the clock on that system.
05
The deck
Walked deliberately, feeling for the softness that means sheathing has taken on water, and noting what the deck is: plywood, or the board sheathing common on the region’s older houses, which behaves differently and fastens differently. Any honest replacement quote states what happens when bad decking is found, at what price per sheet, before the tear-off starts — not after the house is open.
06
The context
What the rest of the street is doing is free information. A subdivision built in one stretch got one generation of roofs from a small number of builders, and their failure pattern is a preview of yours. So is the history of the individual house: previous repairs, whether they were done by someone who understood the assembly, and whether anything has been changed on the roof since it was built.