Yea you need to sand that ll down and add some cloth and re sand. Then Marine Tex or Gel coat.
As far as the trailer goes, you might have to raise the bunks, as the thing looks like it just rests on the beams?
Put the trailer deeper in the water and float above the trailer, hook to stop and pull out slowly, let it come to rest on the trailer this way you are not winching it up and hitting the trailer.
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1986 V20 
Old Fishermen never die, we just SMELL that way!!
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