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Roof needs repair

The roof on my house has a leak. House is a standard 1940's weatherboard with concrete tile roof and a steep pitch. House is about 90sqm. A small amount of water came through on the kitchen floor after some rain recently. This is very near to a leak I had roughly 8 years ago which was repaired with silicone. 2 years ago I had a bigger leak into a bedroom from a cracked tile, this was also repaired with silicone. The roof has two valleys, one of those looks like it has rust from the colour of the metal. There is also quite a bit of debris in the valley which I've been told is from the pointing.