When patching stops being worth it

Daylight or damp in the attic

Go up on a bright day with the lights off. Pinpoints of daylight through the deck, dark staining on the sheathing, damp insulation or rust running down a nail shank all say water is getting in and has been for a while.

Sagging along a line

Straight lines going wavy means something underneath has softened. That is no longer a roofing question with a cheap answer.

Shingles that curl, cup or go brittle

Look along the roof from the ground at a low angle rather than straight on. Edges that lift, corners that curl upward and a surface that no longer lies flat all mean the material has lost its flexibility. Brittle shingles crack when walked on, which is why contractors stop wanting to walk them.

The age on the paperwork

If the roof is over twenty years old and made of asphalt, an inspection is worth doing whether or not it is leaking. The failure modes above are much cheaper to catch before the water arrives than after.

Repeated repairs in different places

One leak is an event. Three leaks in three different areas inside two years is a pattern, and the pattern means the covering has reached the end of its service life rather than suffered a specific failure.

Granules in the gutter

Asphalt shingles are protected by a granular surface. When that surface starts washing off in quantity, the mat underneath is exposed to ultraviolet and the clock speeds up sharply. A handful of granules after a new roof is normal shedding. Cupfuls, years later, is not.

In short

None of these on their own settles it. Two together usually do. An inspection costs little and removes the guesswork entirely.