I figured you would know it was me!
I don't have a lot of time to reply, since today is my first day back at work after a week off.
Some quick points to address your comments / questions:
a) I only have one layer of asphalt shingles on the roof now, so a new layer is possible assuming they don't find any flaws.
Some individual shingles are not lying completely flat (i.e. slightly warped, for lack of a better term), but the roof itself is (level).
I have not
detected any leaks in the attic, but want to be proactive and not wait till something does happen, considering the age of the shingles (18 1/2 years).
b) The chimney does not have flashing right now; there was only roof tar.
However, when they re-did the chimney thoroughly last year, with mesh all the way down to the roof, any and all leaking stopped.
I was waiting for the roof to be redone - i.e. now - to get proper chimney flashing installed, rather than have to do it twice.
4) A few of the roof wooden roof boards / planks have those natural (somewhat oval) holes in them; is that an issue? I assume not since the shingles are supposed to protect the roof and one shouldn't rely on the wood underneath for protection anyway, right?
In any case, I am going to call some contractors today.
If any of you knows of good companies in Northern NJ, feel free to post
I'll update more this afternoon or evening.