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There are a number of different ways you could make OSB water resistant or waterproof but the cost would probably be more than using pressure treated plywood to begin with. Since it has so many crevases if you put many coats of oil based enamel on it, it would be water resistant. You could coat it with fiberglass and use it for a boat. It would be waterproof.
 

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The easiest method would be to keep the dog house in the garage.

Seriously, there is no "easy" method. It is just not a material designed to be used in an environment where it is exposed to the weather.

George
 
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