Repair of the Holes
I made the repair and we successfully re-stepped the mast a few weeks ago.
As requested, I'll provide a summary. 

I opted to fill the holes with epoxy. This decision was based primarily on
the advice to consider the possibility of rotational torque (should
something go awry while raising or lowering the mast) and the feedback that
only one owner had experienced significant damage to the cabin top after
making this sort of repair. However, I did NOT make the holes larger in
diameter below the fiberglass. That is, the new epoxy plugs should not take
much fiberglass with them should they pull out of the wood block. I did
scrape the very small amount of soft wood off the edges of the holes; there
did not seem to be any evidence of water infiltration; the wood block below
the fiberglass seemed very solid. 

I opted to stay with the 1” screws and used JB Weld epoxy. I don't have much
experience with epoxy, and was pleased to discover that I had about 5
minutes to work with the liquid epoxy before it ceased to flow well. I taped
off the area immediately around each of the holes to prevent any unwanted
epoxy from getting on the gelcoat. I did not fill the holes flush with the
top of the gelcoat, but more like up to the approximate top of the
fiberglass.

While the epoxy was starting to setup (about 10 minutes after I had filled
the holes), and using the tabernacle plate as a guide, I put a small piece
of spaghetti in the center of each of the epoxy-filled holes reasoning that
these would provide a good guide for the drill bit. I let the epoxy harden
for about 3 hours then snapped the tops off the spaghetti pieces and drilled
out the pasta with a small bit giving me a precisely-located pilot hole. I
then ran a larger bit into the holes and gently threaded the screws into the
holes to tap the epoxy before it got really hard. I then backed the screws
out and let the epoxy cure for a day before attaching the plate with the
screws.

A few days later the mast raising went well. Since we were still on the
water, we picked a calm morning with minimal boat traffic. All went really
well until the mast was vertical when my mate noticed that the genoa was on
the wrong side of the spreader and was routed through the triangle bordered
by the mast, the upper shroud, and the spreader. When I had replaced the
upper shroud, I had locked the bottom half of the genoa on the aft side of
the spreader. I was told that we were not lowering the mast to correct the
problem … find another solution. I was pleased to find that a 7' ladder
placed on the cabin top and tied securely to the mast allowed me to climb up
and easily remove the pin from the base of the spreader, pull the spreader
out of its seat, move the genoa forward of the spreader, and replace the
spreader and pin. I was up on the ladder less than 5 minutes. I was
surprised how comfortable it was.

Another note: The rigger who built the new shrouds recommended that
replacement shrouds be up-sized to 5/32 inch from the standard 1/8 inch. He
is very familiar with the regular winds that we get in this area and thought
that 1/8 was too small. 

I've attached some photos showing the progress of the repair. I also
attached a screen-shot of the output from the weather station located near
the boat. It shows the 73 mph gust that broke the upper  shroud and damaged
a lower aft shroud. As you can see, it was an unusual gust in that wind
speed went suddenly from about 15 mph to 73 mph.

One final round of thanks to all who provided input in helping me fix this
problem and get back on the water. We've since had a few really good
afternoons on Little Egg Harbor.

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Long Beach Island
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