I would have done this a bit simpler and drilled a 1" hole. Tape one side and fill well with thickened epoxy, making sure you get a solid fill inside the hull to bind to the hull/deck and spread loads. When dry, I would do a smaller hole in the thickened epoxy for the line. Regular 5mm dynema/spectra will do nicely, and I would be more concerned about wear on the line than on the epoxy.
This is the way our Tornado is done, and it works very well.