New York 1950s home, fairly large holes bored into cedar shingles… woodpecker? Bees?
The holes are only in the shingles, don’t penetrate any deeper.
Woodpeckers…
Believe it or not but a plastic owl placed near there will scare the peckers away. I did it on a cedar log home that I built.
Hope this helps. 
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Wow! Could be Carpenter bees and Wood Peckers.
My vote is woodpeckers.
I was1st thinking carpenter bees but the closeup stopped that idea. Doesn’t look like insect damage.
I tended to agree it’s not insects. I guess I was wondering how a woodpecker pokes holes when there’s no place for the bird to perch on a flat shingle… just googled the little peckers and saw this! Thanks all!
Yes!
And the roof is beyond its useful life…IMHO…Yep!
Dang I should try that! Seems a 20 Ga with birdshot doesn’t help much. Puts to many holes in the trees as well. 
Manny ! A 22 works better…Yep!
I have to place flippin’ pinwheels here at my place to keep the peckers at bay!
It worked so well on my log home that I called the many other log home owners that I had built for and let them in on the little secret, The were happy!
Thanks Larry - I will definitely use your idea.
Woodpeckers.
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Thank you!
I feel a Question Of The Week is coming from that. 
In CO, that works for a couple of weeks, max. After that they’re perching on the plastic owl’s heads.
That kind of damage would be from woodpeckers looking for food… bugs. Not excavating nesting cavities or pounding for a mate (they like to do that on metal ducts that extend above the roof).
There’s no cure I know of for woodpeckers hunting bugs. I’ve never seen that kind of damage in CO. If they make nesting holes (common everywhere), recommend installing a nesting box directly over repaired holes. Scare tactics of any kind do not work for long.
I have keep them off my front columns with pinwheels. Fake owls and snakes didn’t work now after 3 years with the pinwheels no more pecker damage.
try one of these, I didn’t see any birds for blocks from this house
Roof is shot anyway and probably had insects. Woodpeckers will peck away at metal flashing to attract mates. Sounds like someone drilling on the house with a hammer drill.
I’ve seen woodpeckers perched on the head of our plastic owl. They work for a while, but in CO anyway, everything gets used to them after a while.
I found that if I moved the plastic owls around every few days or week, that the woodpeckers moved on and didn’t come back for a year or two. YMMV
LOL Larry. I like your method of using a shotgun!
So much damage from woodpeckers here in Northern Michigan and other places I’m sure.
The cluster flies often get behind wood siding and vibrate the building paper. A biologist indicated wood peckers hear that from as much as 1/2 mile away!