Last year our roof was replaced with GAF Timberline architectural
shingles. One of the reasons we had the roof replaced was old aluminum
pans had been installed years ago to prevent ice damming, and the pans
were just nailed on from the top, so water leaked in through the
nailholes. Thank goodness we wouldn't have to worry about that anymore.

This year we had our house painted by whom we thought was a reputable
painting firm. As part of the painting, several small pieces of wood
needed to be replaced at the house corners, due to rot concerns. The
painting company said that they do this type of minor carpentry work,
which also included getting under the drip edges to access the wood,
remove, and replace.

After the conclusion of the painting job, I happened to notice that they
had actually put nails *through* my new shingles in several places. In
some areas the nails were under the preceding shingle (but still nowhere
near the GAF nail line) but in others the nail was just put right
through the shingle from the top, and there are even a few small holes
that are quite larger than a nail diameter.

Yikes! Needless to say I am not happy and unfortunately the final
payment has been made. Nevertheless, I intend to ask the painter to pay
for the repairs. Coincidentally, we've noticed that a roof gas vent
leaks a tiny amount in very hard rain, so I will need to get the roofing
company (a GAF "Master Elite" company) to ensure that this solved. I
intend to ask them to fix the painter's screw-ups too, and then I'll
just forward that bill to the painter. If they balk, my lawyer is ready
to help me and complaints will be made to the BBB and my state as well.
I was mildly annoyed at the painter for being sloppy in some other
aspects, but that was resolved and pales in comparison to holes in my
brand new beautiful roof. :-(

Is this a good approach? Where there are holes in the shingle near the
bottom of the roof near the edge, what is the proper way to repair it
without making it worse? Help!

Thanks for any advice.