I can't tell much from your pictures. But I think I know what happened.
I have a 1998 Bayliner bowrider: where a cuddy has a V berth, I have two
seats with storage underneath. I also have a small storage space in the bow.
All three storage spaces drain into the water ski compartment. The waterski
compartment drains into the bilge. When my boat is on the trailer, the
lowest part is towards the forward end of the water ski compartment. When I
take any water on board, or get water inside while washing down, there is
always about 1" of water in there. I have to extend the jack stand to it's
limit to drain it.
I suspect your cuddy is very similar in design and that the drain is
blocked, obstructing a free flow of water to the bilge where it can be
drained or pumped overboard. I check mine periodically with a fish tape, the
kind used for pulling electrical wires through walls and ceilings. It
doesn't take much in the way of leaf particles, dirt and sand to block the
drain. It doesn't take much to clear them, either.
Hopefully, any wood in the bottom of the boat is still well covered with
fiberglass and protected from the water. At least part of the floor of the
cuddy must be damaged from years of water, but it may not be that difficult
to cut away the damaged part and replace it.

"Ree-Yees" wrote in message
...
I have begun the examination of the small leak when my boat has a normal
amount of water down underneath that the plug drians out.

Here is a view of the step down area with the ruined carpet from always
being wet:
http://home.comcast.net/~ree-yees/100_0406.jpg
The water is leaking out from around this board. It did have screws in
it.

Here is another view from inside the cuddy:
http://home.comcast.net/~ree-yees/100_0407.jpg

Now here is the shoker of whats under that board, a big opening!
http://home.comcast.net/~ree-yees/100_0410.jpg
That is a TUBE your seeing to move water from the back of the boat to the
front I guess but this is obviously where my leak is coming from.

When I tip my boat forward and there is water underneath it must splash up
from here.

Here is a closeup of that area:
http://home.comcast.net/~ree-yees/100_0409.jpg

What do you guys recomend? Should I plug that pipe or should I sea up the
hole with something better than a board?

--Cameron