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My first boat, in the late 1970's, was an outboard with the plug that goes in from the outside. I backed it and the trailer in the water a few times without putting the plug in. Once I just pulled it back out and let it drain and then put the plug in and backed it back in.That's the kind shit I would do if I bought a new toy. I always fuck some shit up in the beginning.
When I got my fishing boat, I probably forgot about the plug at least a half dozen times in the first 2 dozen trips.
The bad time though we were already underway and the boat started filling up with water. So I had to cruise around while it drained, then stop and jump out real quick and put the plug in.