Roof leak repairs

During this home inspection we noticed a few water stains on the 1st floor, then directly above on the 2nd floor and yes, then on the 3rd floor which turned out to be directly below the chimney.

This is a water front property and it was impossible to get a ladder up 4 stories and our drone is not flying. This is what we found in the attic.

F.Y.I. Using silicone in the attic to stop water leaks does not work! I am not sure what this handyman was thinking.