Fixing a badly made shiplap building - reusing boards?

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I moved into my current home a couple of year ago and it's got a timber outbuilding attached to the side of the house. A decent sized space but poorly constructed.

Following a couple of leaks I started investigating to find theres no membrane between the shiplap cladding and OSB, which isn't ideal when I'm looking to insulate it and make use of the space.

If I were to take the cladding off to add the membrane am I likely going to be able to reuse the boards or is it generally a case of they are likely to become too damaged in the removal process? I already know the lower ones need replacing as theres been some water ingress at the floor level, resulting in damage to the OSB so do plan on replacing those at the very least but ideally dont want the monumental expense of redoing the whole building if I can avoid it.

And if anyone knows of some magical product I could apply to these to seal them up and avoid having to do the membrane at all, please do let me know!
 
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