When we purchased the house, we knew that there was two holes in the roof. One in the main roof over the blue room and one in the dining room roof which was part of the kitchen/dining room addition.
The hole on the main roof was not too bad and just needed some new shingles to be put on there. The challenge was getting up there to fix with no scaffolding.
Here are the pictures from the roof on the dining room getting fixed. Apologies if some are duplicated.