In alt.home.repair, on Sat, 25 Jan 2020 13:03:47 -0500, Gary
wrote:

micky wrote:

If it's the caulk, it's been there for 13 years. How come no drip into
the 2nd floor until this year?

What I see in that picture... weep holes are clear. It's the bad
caulking between shingles and flashing. All those gaps will let
water in. Where the roof is buckled, I see no caulking at all.

I would get someone up there to recaulk that line asap. Fix the
buckled part later if you want to wait. For now, stop the leaks.
Recaulk it and check the other side too.

Note: No caulking outside will hold up for 13 years. With an
important thing like a roof, get that caulking checked and
repaired once a year or two.

Thanks, Gary (and everyone). When you guys disagree, i'm not sure what
to say, but I'm glad to hear all everything

It's enough that I'm not fully trusting what the first roofer said. So
I'll see what the second guy says. The guy coming on Monday charges $60
for each replacement sheet of plywood, but I don't know what the main
charge will be.

There are other pictures, but mostly plywood. This one is the ridge
rail but it's probably the front of the house when the leak is in the
rear. I wish it would rain so I could go up there and watch it in
action.

First picture, repeated:
https://static.companycam.com/lambda...eg?d=2880x2880

I think this is just a close-up of the problem area on the right of the
first picture.
https://static.companycam.com/lambda...eg?d=2880x2880

BTW, it kept raining when he was doing the roof and he would diligently
tarp the roof and come back the next day, 4 days total I think. And he
tarped the grass and I found only 2 or 3 pieces of roof in the grass
after he left. So he still gets a lot of points. I wonder if he maybe
he taught himself how to do a roof and didn't know some things. His
mother did the booking. I called a few years later for a different task
and she said he didn't do that, and I can't remember the rest.