Most every boat I've seen had their drain plug go in from the outside. And that is because the pressure of the lake water (or river, ocean whatever) presses against that plug pushing it in towards the inside of the boat. So no need for any type plug installed front the inside. If an inside plug was the only plug keeping out the water thought the drain hole, the pressure would probably push it out eventually, unless it was threaded in. As for the through hull hole for the drain, it has to be totally dried out like previous commenters stated and then sealed with some very good water proofing substance and/or brass, PVC, stainless steel or something to that effect to keep water from ever again reaching the transom wood material. Otherwise you will be replacing your transom, and soon too... In fact if it has been wet since manufactured because of lack of a proper drain hole tube, you better really look it over now to see what damage has already taken place to the transom. Sitting wet wood doesn't take very long to rot...