Siding repair on unique shingle siding

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Attached is a photo of the siding in question; on the rear of the house the corner is splitting badly near the bottom and I'm beginning to get some minor water marks on the interior wall below. I'm wondering if I can pick up some red cedar shingles and match the style with the short/long overlap. The house is 100 years old and the first floor has no sheathing so I'm not entirely sure what I'm going to find when I start pulling off the existing siding. Is there anything I should prepare for such as flashing where the siding meets the shingles?

Thanks!
 

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