I'm having a hard time with picturing your boat being difficult to trailer. If the winch is properly greased and the bow eye and winch are set up at the right height, the thing should be ridiculously easy. Make sure the winch line is slightly higher that the bow eye. Marine Tex was already mentioned for the screws. The stuff is expensive, but it is a really good epoxy. I have repaired broken transfer cases (yes, plural) with no leaks after repair. I always have a can on hand.