I see. On my 16 the holes through which the shroud anchors go are only through the top lip of the hull, meaning that there is no place for the water to actually get into the hull through that hole. I wonder if yours have worn through the inside edge and have made a small hole clear through the fiberglass. If you back out the shroud anchors, can you see into the hull? If so, it may be time for some fiberglass and epoxy repairs... As far as the bridle anchors in the bows of the boat, mine have swiveled around and worn out a bit of the gelcoat. If it bothers you I suppose you could put some washers between the clip and the fiberglass, or maybe silicone them into place so the holes don't get any bigger. If you order the Hobie Catalog the last 15 or so pages contain the exploded diagrams and part numbers for all their boats.
jrg