We start above the ceiling, not on the shingles
Before anyone climbs a ladder, Duncan usually pokes his head into the attic first, because the underside of a roof deck tells a different story than the shingles ever will. Dark staining along a rafter, insulation that has gone flat and damp in one corner, or daylight coming through a nail hole all point to a problem before we have looked at a single shingle.
Ventilation gets checked at the same time. A roof that traps warm, moist air underneath the deck ages from the inside as well as the outside, and no amount of good shingle work on top fixes a deck that is rotting from below because the attic never gets to breathe properly.
What we look for once we are actually on the roof
On the surface, we are looking past the obvious missing or curled shingles to the details that predict where the next leak will come from. Flashing around chimneys, skylights, and any place two roof planes meet gets checked closely, since a flashing failure causes far more leaks than a worn shingle field ever does.
Granule loss collecting in the gutter, soft spots underfoot on the plywood deck, and nail heads sitting proud of the shingle surface all get noted, because each one changes what the job actually needs rather than what a quick look from the ground would suggest.
The questions that change the price the most
Whether the existing deck can be reused or needs replacing is usually the single biggest swing in a quote, and we will not know that for certain until a section of the old roofing comes off. A soft, spongy deck under a patch of moss covered shingles is common enough that we always build a contingency into the conversation rather than promising a fixed number before we have opened the roof up.
Whether the job needs a full tear off or can go over an existing single layer, how many valleys and penetrations the roofline actually has, and whether the attic needs added ventilation as part of the work all factor into the final scope, and we walk through each one with the homeowner before anything is signed.
What we hand over before any work starts
A quote from us spells out the actual materials by name, the number of layers coming off, whether decking replacement is included as an allowance or priced separately if it is needed, and roughly how many days the crew expects to be on site. We would rather a homeowner ask questions about a specific line item than sign something vague and find out later what it did not cover.