How to tell a roof needs replacing, not patching
Most roofs give plenty of warning before they fail. The trouble is that the warnings look like small problems, so they get patched one at a time until the patches cost more than the replacement would have.
Granules in the gutters are the clearest signal. Asphalt shingles shed their surface as they age, and once that surface is gone the mat underneath weathers quickly.
If two of these are true at once, get a second opinion before paying for another repair.