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I wouldn't be without a bilge pump in my Montauk. Exiting the channels from inland lakes to Lake Michigan, the exit is very crowded and can get very choppy, especially on a windy day. Then some idiot with a huge Cigarette boat slams open the throttles in front of you, leaving a huge hole in the water, and you suddenly have green water coming in over the bow. I had so much water in my boat, I doubt I could have gotten it up on plane to drain it by removing the plug. And I wouldn't have wanted to get up on plane with several drenched teenage girls jumping around grabbing towels and saving their IPods. The bilge pump handled it fairly quickly. I now make sure to have passengers come aft while exiting the channel on all but the smoothest days, to keep the bow light.

I would definitely run the drain over the transom. I use a piece of clear plastic tubing, secured with plastic wire ties. I always flip it on for a few seconds before I start the motor, to make sure I can hear that it is working, having once blown a fuse because of a worn out switch. Also, I routinely check the tunnel where it is mounted to make sure there is no debris that could block the pump.