Thanks Tim, you were correct, Missing something so ridiculously obvious at the time!
Mister don't run with the scissors here (you know the guy who usually gets stabbed when the person running with the scissors turns to ask why they shouldn't run with a pair of scissors in their hand).
When I got my current boat which had been sitting for years unattended I started by replacing the rigging but then got my phone and stuck my arm in every access point and snapped pictures of every place I could and could not see reviewing them on a computer monitor enlarged and brightened. Things that looked questionable in any fashion were removed and re-bedded at the least with some replaced. Mine is a picnic boat so it was even harder to inspect under the cockpit with very few inspection ports and no lazeretts that one could open. Having an in transom rudder that exited the hull below the water line I cleaned up the seal area on that, replaced the bedding and added a collar outside where it exited the hull to give it even more sealing area and to reinforce it. After I washed out the bilges I put the bilge plug in, filled the boat to the water line with fresh water and inspected for any drips or damp areas on the outside of the hull and found none. Water did not come out of the cockpit scupper thu-hull when there was only water in the bilge which is as it should be.
When launch day finally came I put it out and tied it to the dock for a few hours while I inspected for any leaks or seepage and finding none then I buddied up with a well seasoned sailor and we took the boat out for a trial and the only event was that 2 senior citizens went out sailing a 15 picnic boat in 15 mph winds coming back with smiles on their faces.
I believe you learned that you have to inspect and double check every hose and fitting on that hull and probably have some bedding and old hose to replace along with some corrections of questionable repairs done by previous owners and possibly a through hull to replace. Each spring when you get the boat ready for the water you will need to inspect those hoses and thu-hulls again. On first launch of the season allow time for the boat to sit at the dock for enough time to inspect for water coming in. Be mindful that plugging a thru-hull that's not bedded correctly is not going to stop it from leaking between it and the hull. Also make regular checks of the centerboard trunk along with the centerboard cable seal, pivot and lock pin areas for leaking or fracturing. Also check the leading edge of the centerboard trunk for any signs of damage as many times the centerboard can slam that area and crack the glass.
Continue inspecting and be mindful of how things are supposed to work and don't arbitrarily start plugging everything as you may find yourself doing a lot of bailing when water splashes in the boat. Its not a lot of fun when a self bailing cockpit doesn't drain and every bit of water that splashes over the bow or rail just builds up around your feet. Note that a water scoop made out of an old bleach bottle (milk bottles are too flimsy) can be a wonderful thing to have on board just in case.
Have fun with it and I believe most here will be looking forward to when you report you've found and slayed the dragon.