Well, the roofer (highly recommended by Angies List) came by to take a look today and I’ve got good news and bad news.
The good news is that both the leaks we found are extremely common and easily repaired. The one tha alerted me to the problem via the bedroom ceiling is likely from the chimney flashing. The one in the “middle of the floor” is likely from the flashing where the roof hip meets the dormer.
Also in the good news category, the roofer leaned out the attic window and took a close look at our roof and said that it’s probably about ten years old and that we should easily get another ten years out of it. This is great news as we’re planning on putting an entirely new roof (architectural shingle or slate or tile or something) on when we do the addition).
The bad news was that he’s booked until Thanksgiving. He said he saw no “red flags” and that we should be OK for the next month, so I’m going to keep an eye on things in the attic and keep my fingers crossed.
Oh, and lastly, the first thing the roofer mentioned to me when he came in was that his company has done roof repairs on our house before (likely in the last 4-5 years). Small world.