Re: Leave drain plug out?
Note that there is a difference between a boat with a self-bailing DECK, and a boat with a self-bailing HULL. My 16' Wahoo has a self-bailing DECK, but it also has a bilge under the deck like a normal boat that is not self-bailing.
Most Whalers don't have a bilge under the deck because that area is totally filled with foam. I think with most Whalers, you can leave out the deck drain plug, and it will self-bail. That would be considered to be a true self-bailing HULL.
Since my boat has a self-bailing deck, I should be able to leave the deck drain out while docked, and all the rain water should exit thru that drain. In reality, some of my deck PVC drain pipes are cracked, so rain water collects in the bilge like a normal non-self-bailing boat.
If the the OP stickball's boat is like mine, I suspect that some of the forward deck drain fittings are cracked. This would allow him to drive the boat with the deck drain plug out with no problems, but would still allow rainwater to seep thru the forward cracked deck drains into the bilge while docked.
Here's a cutaway of my boat from a 1990 Wahoo brochure. If you embiggen the picture, you can see the two drain plugs.
I posted the rest of the Wahoo brochure here:
http://forums.iboats.com/showthread.php?t=444988
Unfortunately, it doesn't show the OP's 21' Wahoo.