The short answer
Thick masonry walls carry a roof for generations, so the trouble is rarely the wall. It starts where the covering meets something else: a gable verge, a chimney, a wall plate. Repairs on these houses follow the wall, matching the mortar and the line of the roof as it now stands.
Thick walls of flint and sarsen, or old brick, were built to carry a roof for generations, and the roof above them has a different life from the wall. A heavy covering on solid masonry rarely fails because of the masonry. It fails at the places where the covering meets something else.
Q1.1Where does water get in between wall and roof?
A verge, where the slope finishes against the top of a gable wall, is the first place to look on a flint or stone gable. The covering is pointed into the wall top, and once that pointing cracks, water tracks beneath the edge tiles and down into the masonry. The same goes for flashings, the strips of lead or other metal that seal the line between slope and masonry. Lead lasts a long time, but it tires at joints and corners, and a strip that has curled up at one end may be letting water in along its length.
On old cottages the wall plate, the timber that spreads the roof's load along the top of a wall, can sit deep in damp masonry. A slow leak over many winters shows up there first as soft timber, long before anything is visible indoors.
Q1.2Which mortar suits a flint or sarsen verge?
Pointing flint and sarsen with the wrong mortar can trap damp in the wall, which is why the mortar at a verge or chimney is matched to the wall rather than chosen for being hard. Older houses also have a covering that has moved with the timbers over the years, so a repair follows the roof as it is rather than forcing it flat.
Our roof repairs page explains how a small fault is told apart from a failing roof, and the chimney repairs page covers the stacks where wall-and-roof leaks often begin.
The survey photographs show each junction close up, so you can see the cracked pointing or the lifted flashing for yourself before deciding what to do.