Just saw this last night. I really enjoyed it, but I have a long list of things I would have done different if I were in the same situations.
I think where the real truth of it lies, is that his circumstance progresses through a series of unfortunate events, not just one, and those situations are the ones that are hardest to predict and prepare for.
Without real spoilers, I think I can say this movie is not really about sailing.
Now, my .02 on the main issues:
Hole - Plywood from interior cabinet work(bunk,chart table, etc), 5200 fast set, installed and bolstered from the inside, done. Worry about fiberglass when you get to port.
Pump - If you've got good batteries, you've got to get an electric bilge pump setup and working, even if you have to run it from the cockpit with hose. This is why I like the idea of a portable high output electric pump so much.