Smart fella.
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When I lived in Texas I had a fiberglass boat that was almost impossible to get the plug in from the inside, as you had to reach your whole arm length to insert it and then to tighten it. I installed an automatic plug that had a small cage with a plastic ball in it that would seal the drain hole when the boat was in the water. The great thing about it was it would drain any water in the bilge when the boat got up on plane. Similar to the one below:
Auto Drain Pluug
There are others like this one also:
Metal Automatic Drain Plug
My late Dad lived on the water, and He liked to put His fishing boat in during early Spring, and we would pull it out on the trailer after a few frosts that winter. The old aluminum boats would stay in the river tied up to the pier, with the runabout occupying the boat house. Often we would get in the old aluminum boats with rainwater or whatever in the bottom of the boat, many times almost a foot deep. Untie, push out, connect the gas line, prime up the old Evinrude 18 Fastwin, fire it off, and as the boat would start to get up on plane we would reach down inside the back of the boat and snatch out the drain plug. The water would suck out the back hole there like a pump! In fact, we used to keep a piece of rope tied to it to help with pulling it out, with the other end of the rope tied to the back of the boat so we would not lose it, like we did one time!
When I got my first boat with the drain plug on the outside, my first thought was "Well, we won't be pulling that plug out anytime we are up on plane". nonono
I have the plug with the lever and the screw type. Last time out screwed in the screw type from the outside, worked great!