I wanted to relate a story.  I began to notice some water stains on my kitchen ceiling, near where a dormer was added in 1999.  It took two months before I could get a roofer to come out to look at my roof.  Seems like they have been extra busy since last August 4th.
What happened on August 4th?  For me, I was sitting on Wells beach on vacation, but back home there was the Hail Storm from Hell.  Sure enough, the roofer told me that my roof and flashing were damaged by the storm.
Thursday the insurance adjuster came by and got up on my roof.  He said that not only was recommending that my whole roof be replaced, my metal gutters and two downspouts needed replaced too, and my kitchen and dining room ceilings needed repainting too.
So does this mean anything for you?  I can't say but you might consider having your roof checked before the winter. BTW, the roofer who I finally got to come by was Pellegrino Construction 617-299-8526, I spoke with Tyrone 516-937-8013 and found him to be very helpful.