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I fon't understand the drywall over shiplap? It looks like someone decided to hang drywall over existing and decided not to remove anything and "just cover it up" so you ended up with layers and layers of finish wall on top of each other. If you are just repairing that section then there's really no reason to remove the drywall which adds to the overall cost and more importantly your labor. If you decided to remove it, then I suggest removing the entire wall from corner to corner to see what's behind there and plan according from that point. I bet you will open a can of worm. There's always something else to fixed once walls are opened up. If there isn't anything else going on but a few holes from staples or nails, then just patch, paint and enjoy until something comes up like a leak from the window or something else then tear it open and perform the necessary repairs. Unless you really enjoy home repair, you will become a slave to an old home.
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