When we bought Morning Wings, nee Sea Hawk, we contacted Newport Offshore Yachts who were building the Downeast boats again. I was checking on blisters we found after being hit by lightening. I was fortunate enough to talk to Powells original superintendant. I was interested in possible bubbles in the Gel coat instead of blisters. Turned out this had been a problem in manufacturing. I also questioned the strength of the bob stay fitting as I was planning to connect a shackle and block for an anchor spring line. He advised me not to worry as the hull was sound and the fitting added after layup and then glassed in. I too have had problems with any style caulk refusing to remain in place. Now trying 3M 101. I my opinion if you were to replace the whole fitting I would do it from the inside carefully grinding away the sealing fiberglass and then knocking the fitting back into the hull. Just be sure to wear masks when working in the locker and suggest using a hooka gear for breathing so you will live longer than S-A me.