My opinion: If everything is dry for you and the water drains smoothly through your drainage, stay calm and all is well. He built an extension and then took care of the connection between the roof and facade himself. It is, of course, hard for him now to admit that he might have done something wrong. But when I see the amount of silicone, I do not assume that the connection was done correctly. If he really just sealed the gap with the sheet metal and masses of silicone, the error will likely be right there. Silicone is simply not suitable for a permanent seal but must be renewed from time to time. Probably this time has now arrived or is overdue. Correctly, he should have connected to your roof sealing back then and, for example, pulled a roofing membrane up onto his house. Only then the metal strip should have been placed on the roofing membrane to secure it against detachment and similar issues. But this is just my layman's opinion, describing how I would have executed the detail.