Now, I've had another piece of deck hardware pull out on two different boats. I liked that the first boat had no inspection port, so I cut through the deck. (Mistakes were made, which I'll address later).
With this second boat, if I don't cut access through the.bottom, I'll cut through the side. That repair has to wait until Spring.
What I think is happening, is the halyard has worn the plastic mast-top fitting so the halyard is being cut by the edge of the aluminum mast. That cutting resistance requires more force to raise the sail--increasing the loading on the fairlead. (Which has pulled out).
I would reposition about 1/2" away from the original holes in the deck. Drill pilot holes just through the fiberglass deck and probe with a pick to see if you have sound wood (backing plate) under the deck. If good, drill small pilot holes in the wood backing plate, coat your screws in epoxy, screw on the cleat and let cure. Fill the old screw holes with the epoxy goop of your choice and go sailing.
If the backer plate is all rotted or has fallen off and into the bilge, you will need to install a deck port and and epoxy on a new backer plate.
p.s. Unrelated. The bomb cyclone winter storm here in the "almost Canada" east lived up to all the Weather Channel hype. It was a kicker
with the most rapid temp. drop in decades. Buffalo, NY is still not out of the woods yet.
I do not have a lot of experience, but so far everyone that pulled the screws the wood was bad.
I cut the hole and put an aluminum backing plate and stainless machine screws with self locking nuts. I have done this to 3 or 4 hulls so far. Oh and usually all the other wood is bad too. That is you need to try and tighten all the screws on the deck. So far all would just continue to spin and not pull to a stop.