Johnny,
OK, first, your leaky livewell drain. Most likely, it is a 1 1/2" drain. It is also an elbow. Apparently the hose to barb connection is leaking as the incoming water never seems to make it into the livewell. Can you reach and get the hose off the barb? Could be easier said than done. Also can you reach the thru-hull on the hull side? There are 2 reasons I ask this, because there are 2 fixes. Or maybe 3. First, and most likely the easiest, is to try and tighten the hose clamps at both ends of the hose. Second, the hose could be split at the drain, and thus needs to come off there. That's where this little device from
T-H Marine. Insert this inline scupper into the hose going to the t/hull and a new section of hose going to your drain. I wouldn't want to lose the use of your livewell due to future resale considerations. However, the third, and most drastic is, if you can reach and remove your t/hull, this little guy from
Marine East. Install that in you t/hull hole and never worry about it again.
Now for your list. If you have her on a trailer, pull the garboard drain plug (that's a fancy name for your "buttplug"), raise the bow considerably, and see what comes out. All you stringers should have weep holes in them that allow any trapped water to eventually drain into the aft bilge. Hopefully it is simply some water trapped in a stringer compartment that hasn't had a chance to make it's way back to the bilge.