So, I'm going to reply to this 2 year old thread with some information and what I've learned for the sake of reference. Looking back, I was quite green. Now I'm just sorta teal, but with 2 seasons under my belt, I've got a much better idea what I'm doing. So, we trailer sailed the boat in the summer of 19. Midway through that season, we took some friends out with us and found that with the boat sitting low in the water, we were picking up a ton of water in the bilge, and draining into the cabin. I realized that the cockpit drain was sitting below the water level and so then checked the cockpit drain tube, which, it turns out, had failed on the underside and was the culprit. We replaced both the drain hose and the through hull fitting, sealed with 5200 and it has been perfect since. At the end of the season, it was clear that the deck fittings needed to be resealed so this spring, we rebedded everything with butyl tape and had the windows on the hatch removed, replaced and resealed. It turns out those still have a drip in them, but everything else has been great.
We had the boat in a slip in Bayport on the Great South Bay from May until mid November. The bilge was pretty much dry all year and only had a little moisture after pretty heavy rain. I think that problem is from the 4" deck plate in the cockpit floor not having a gasket in it. I've got a replacement that I'll put in this winter or next spring. The small amount of water, (about a gallon) in the bilge that came forward when I backed the boat into my sloped driveway a week ago was easily removed by sticking my shop vac nozzle into the bilge. It's now bone dry.
I'm going to remove and reseal the cabin port lights this winter and reseal the small drip in the hatch window, and we should be good to go. Rudy at DR Marine suggested sealing spider cracks in the gelcoat of the cockpit seats and floor with clear epoxy, which I will likely do as well.
This summer, at the end of August, the centerboard uphaul wore out so that I couldn't bring it all the way up or let it all the way down. The outer jacket on the line was bunched up above and below, so we hauled it out and by jacking the boat up off of the trailer, were able to drop the center board and replace the line. If you ever do this, the line that comes from DR Marine is about 5 feet too long, and when I let it out the first time after relaunch, the line went all the way out and wrapped around the centerboard. I didn't realize it at the time, and it caused the board to wedge in the trunk. Luckily, when I realized, I had a tail wind and decent waves, to after a few splashes, it shook loose. We retracted it as far as it would go lightly then anchored behind a jetty on the next mild day and I was able to reach under the boat with my foot while holding the rub rail and guide the line over the end of the centerboard and my wife kept it under tension until I was back onboard. An adventure, but better avoided, I'd say. A word to the wise.