I own a 96 Sailfish CC 18'6

So today was awfully crappy.... Get to the boat ramp to find out someone decided to steal the winch handle off my trailer so that was the first thing to piss me off. We finally get the boat off the trailer after pondering for 10-15 minutes on if we should or not and how we would get the boat back on the trailer after we launched it. I come back to a boat taking on a whole lot of water.. very unusual, I was like maybe its heavier today for some reason, but ill get it on plane and itll drain out like usual i was thinking.... I turned the live well on as we pulled out of the boat ramp to keep the shrimp alive, maybe for a couple minutes. Well I try to get the boat to plane but it wouldnt, I was like jesus we must be taking on water or something. I remove teh battery compartment lid and the whole thing is almost underwater. I freak out and turn around back to the boat ramp and run to get the trailer. Pull the boat out of the water and pull the drain plug and it takes the boat like 5-7 minutes to drain out. Decide to put the boat back in the water to see where the water is coming from. I back the trailer not all the way in when my buddy says water is coming back into the boat, I look and its coming out of a hole where the hose for my live well runs through my. the only thing is, I have had a leak in my live well since I have owned the boat, it needs to be recaulked around the seal is all. But I am hesistant to put the boat all the way in the water so I pull the boat out. The only thing that has been messed with since we last used the boat last week is the Scupper. My dad took one off the last time we cleaned it cause the drain was clogged, and maybe he didnt put it back on right or its not working properly? Does anyone know if those have a seal or something that might be broken? I looked at all the hoses that are visible and they seem to be intact and secure. I really am not sure where the water is coming from. There is no cracks in the hull from what I can see and its a fast leak!


Notes:
1. Plug was in the boat
2. Scuppers were only things messed with since the last use
3. Boat was taking on water before the live well was turned on
4. Boat was in the water for about twenty minutes

So I just got done messing around with the boat to figure out where this leak is coming from, and I still dont know.

I filled the hull with water from the hose and there was no visible leaks coming from the thru hull fittings or air bubbles from the hoses.

I pulled the plug and drained the water from the boat.

Then I checked to see if there was a leak in the scupper hoses by running the water hose through the drain holes on the deck and no leaks there either and the water properly drained out on both.

Then I ran the water hose through the live well intake at the back of the boat, and water started coming into the live well. (Is it supposed to fill up? The live wells never fill up on my boat unless I turn on the pump usually) No water was draining through the drain plug but was only coming out through the live well drain, which is the was its supposed to be right?

I ran water directly through the live well drain and it came out the live well drain plug without any leaks apparently.

Heres the only thing about the live well, the previous owner for some reason removed something on the live well and there was about 2 inch circle hole, it looks like its for another pipe or something. well he covered it with something and that came off awhile ago and i covered it with a rubber sheeting and contact cemented it, well now my attempt to fix the problem has failed too and water is leaking through underneath the live well. Only thing is this water DOES NOT drain out anywhere! I cant seem to find where this water goes, you can hear the water in the pipes or draining somewhere but its not visibly coming out outside the boat...

I was thinking maybe i am an idiot and didnt put the drain plug in properly this time??

The only thing I can think of doing is putting the boat back in the water and sumbmerging it all the way and find out if its still leaking

Be careful, that might be your only chance to find it!

Check your bilge pump. Look at the connections (how it is plumbed in fom the inside). Maybe one has broke.

If your livewell is like most others, water comes in through the livewell drain unless the drain plug is in. Water will fill up in the livewell to match outside water level. If the mystery hole (the one you tried to patch) is below outside water level, water could be pouring thru the hole into the hull. Just a thought.

Have seen recently the drain plug put in the livewell hole instead of proper one. That boat filled fast.

Can you explain this a little better im kind of confused on what you mean. do you know how i can figure out where the water drains out from the mystery hole?

I will try to explain what I said, but I could be out in left field with my thinking. The mystery hole sounds like it might have been an overflow or a pump-out. If it sprung a leak somewhere under the floor, the previous owner may have decide to just plug it. When the plug failed, water could be pouring from livewell into the hull as fast as the fill pump trys to fill the livewell. If the mystery hole was a pump-out, it would be in the bottom, and would let water into the hull if the drain plug is not in, even with the fill pump off. I would try plugging the livewell drain and then fill the livewell with the boat out of the water. If you get water in the hull, it has to be a livewell plumbing problem.

so youre suggested plugging the live well, fill it with water from the hose and then what? am i trying to find out if the leak from the mystery hole is leaking into the hull?