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Here's how we approach a replacement like this. Before a single shingle goes down, the deck gets covered with Roofnado StormTread underlayment. It's a heavy-duty synthetic product that creates a solid moisture barrier between the decking and the shingles. If water ever finds its way under the surface - from wind-driven rain, ice, anything - that underlayment is the last line of defense. We don't skip it or go cheap on it.
The chimney work is where a lot of roofers cut corners. A chimney is one of the most common spots for leaks because it's a penetration through the roof - water has multiple ways in if the detailing isn't done right. We built out a fresh wood enclosure and capped it properly so the transition between the chimney and the new roof is tight and clean. No shortcuts there.
The shingles themselves went down in a consistent, tight pattern across the full surface. New vent boots got set properly around the pipe penetrations too - those are small details that matter a lot for keeping the system watertight for years to come. When we do a roof replacement, we're thinking about the whole system, not just what's visible from the street.
A roof done right doesn't need to be revisited for a long time. That's the whole point. Clean materials, solid underlayment, detailed chimney work - that's what gives a homeowner real peace of mind.