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I don't think I would put a hole in my trunk for the exact reason you stated, water/rain.
If you had to do it I would try to make it so you can close the hole when needed. I have seen on older civics where they have a duct in the fornt which allows air in when it is opened. You could put a lever which you moved to open the duct in the truck to let the air in and close it when it is raining or the when the roads are wet.
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