Get the book.....
Don Casey's book "Deck and Hull Repair" was critical for the same project for me. I describes a series of permanent fixes. And get some help when you are lifting off the track so it doesn't bend. We overdrilled the hole, chucked a bent nail in a drill, and cleaned out the surrounding core (see book and this will make sense). We then filled in this "cavity" with epoxy. When it set up & cured, and we drilled a hole to rebed the track, we are virtually assured of no leaks into the core. Be sure to check for core damage while you are in there. For what it's worth, we put in a small backing plate (plywood) along the length of the track. All this on an Oday 28, and it took about two weekends. One to do the "overdrilling" and epoxy, and the other to rebed track. For a temporary fix, I really would not advise caulking the underside of the bolts (in the cabin). Believe me, that if I have water leaking around the bolts, I want it to come into the boat. For starters, I want to see it and know where the leak is. Lastly, I do not want the water to get locked into the core; I want it to run out! Good luck.
