Where roofs actually leak
In a typical year the repair calls from Milford homeowners break down roughly like this: a third are flashing at chimneys, sidewalls and skylights; a quarter are cracked rubber pipe boots that have split after 10 to 12 years in the sun; the rest are wind-lifted shingles, exposed nail heads, blocked valleys and ice dam damage at the eaves.
Almost none of them are a hole in the middle of a shingle field. That matters because a repair aimed at the wet spot on the ceiling is usually 4 to 8 feet downhill from the entry point. Water follows the rafters and the underlayment before it shows up inside.
How the diagnosis works
The first stop is the attic, not the roof. Water stains on the underside of the deck, rusted nail tips and daylight through a gap show the path far more clearly than the shingle surface does. Then the roof is walked, with attention to every penetration uphill of the stain.
Where the source is not obvious, a garden hose test isolates it: water is run on one section at a time, lowest first, while someone watches inside. It takes 30 to 45 minutes and prevents the common mistake of replacing a chimney flashing when the real problem was a boot 6 feet above it.
The repairs themselves
Pipe boots are replaced with a new flashing, not caulked. Step and counter flashing at chimneys is cut and installed new, with the counter flashing let into a mortar joint rather than surface-glued. Lifted shingles are resealed if the seal strip is intact and replaced if the shingle has creased.
Ice dam damage at the eave usually means the first two or three courses come off, the deck is checked, ice barrier is added or extended, and the courses are relaid with new shingle. If the roof never had barrier, that is the moment to add it.
Every repair uses a shingle matched by manufacturer and color where the roof is young enough for the product to still exist. On older discontinued shingles the closest match is shown to the homeowner before it goes on.
Storm and emergency calls
After a nor'easter or a summer thunderstorm with straight-line wind, active leaks are tarped the same day where possible. The tarp is fastened with battens, not just nails through the plastic, so the next front does not take it. The permanent repair follows within days once the deck is dry.
Photos are taken of the damage before the tarp goes on. Insurance adjusters ask for them, and a dated photo of lifted shingles with the storm date is worth more to a claim than any description.
When repair stops making sense
The honest threshold is roughly this: if the repair would cost more than a fifth of a replacement and the roof has less than 5 years left, replacement is the better use of the money. That judgement is written into the repair note so the homeowner can decide with the numbers in front of them.