It appears the problem was due to an issue with how the extension was
installed as an add on after purchase from General Boats.  I got a
replacement tiller extension that has a metal sleeve to provide support to
the connection to the extension.  After putting some some super glue in the
crack and then clamping the tiller with a C clamp, I drilled the larger hole
for the new sleeve by expanding the existing hole.   I also put down some
super glue before inserting the metal sleeve.  I also added two stainless
screws going horizontally through the tiller, a few inches  before and after
the metal sleeve, to help keep the crack from spreading.  Then I added some
x-treme tape as a wrap on either side of the tiller extension to help
provide support and this also provides some extra grip.  The new setup
worked well on the initial sail yesterday.  Hopefully it will hold up!

Photos for reference in case anyone else runs into something like this:
Installation1.jpg
Finished.jpg



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