56" monos are usually pretty deep. I am assuming this is something like an Enforcer mono? If so, I would run the pipe through the transom as high as I can while keeping it in the transom. It most likely will not stick out all that much. Once you find the proper length, you can look into sealing around the pipe with a silicone gromet of some kind if water infiltration is a concern. If its a shallow mono then running out over the transom might be an option. You could also do it with a deep vee, but it will definitely put a lot of weight up high. Just my opinion. Post some pictures of the boat if you can, maybe my opinion will change.

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