Jeremy, assuming you live in a freeze/thaw conditions area, always keep the boat covered with a tarp and always keep the stern and motor board covered to keep moisture away from the motor board/transom junction. The hull/deck seam should be inspected periodically and it should be sealed, particularly in the stern area on the TDB-14s around the stern floatation chambers. This seam sits very near the waterline when the boat is loaded. I am pretty sure this is the site of water intrusion that so often occurs in the floatation chambers. In the TDB-14', the interior deck countours the rocker hull, causing a low spot on the keel where water will pool and sit about two feet aft of the bow storage compartment. A sponge or a hand bilge pump work well to get this waterr back overboard during intervals when you can't drain the boat when you put it back on the trailer, post recovery. Water will move through gelcoat and glass slowly over time, so you might want to consider sanding the deck down and putting a couple layers of Cabelas rubberized texture paint or Tuf-Coat on it, particularly if the boat will sit at mooring after use for a long interval.
Exposing the motor board/transom seam to repeated freeze/thaw cycles only invites water intrusion as the ice phase slowly "chisels" the seam apart during its formation, a millimeter or two at each freeze portion of the cycle...progressing to the point of intrusion, usually around the through-bolt holes that hold the motor board to the transom.
I use gelcoat restorer with a UV inhibitor I purchased through Hamilton Marine on my TDB. It initially dries to a semi-glass finish, so do the application early prior the season to allow it to weather back to the matte finish.
The Clark brothers used oak for their grassing rails through 1994-bad choice of wood type for this application.
