gree2056, I've missed the part where you introduced yourself so, what is your name? Gary Friesen here.
Your friend who will parallel your course, is he a member of this forum too?
Here are a few things you can consider:
Can I reduce sail area when overpowered?
Can the bows and bow tangs handle the additional load from the forward tramp?
Can I recover from a capsize where I go "turtle?"
Shouldn't I have an anchor to safeguard the boat from floating away during an surprising rise in tide?
How to do I make absolute certain that there will always be a totally clean and dry portion of cloth to wipe the oil off of my lenses and the sunblock out of my eyeballs?
When living in a marine environment, salt should be your companion, not the enemy. Learn to live with it. Where I come from, sea water submersion was actually a reasonable treatment of cuts. Yes, antibiotic ointment is far superior.
Don't fill the inside of the hulls up with weight; you'll get in trouble when "turtled."
Consider being able to pitch your tent on top of your trampoline. Fewer flea bites. Air on the underside promotes drying.
Investigate cell phone coverage in the area. Cell service providers should have coverage maps on the www.
File a float plan with somebody who is dedicated to be your information relay, ground support person who will know when they should or should not report you missing or overdue. Have an established protocol for what that ground support person does or does not do in the event that you do or do not contact them at certain times.
Wool socks can save you from blisters, even when wet.
Stand up and exercise the legs every hour to prevent them from going to sleep. (30 squats works for me)
National Geographic "Explorer Paper" will take normal ink jet ink and produce waterproof results. Print your tide charts, boat insurance information, boat registration, copy of your personal identification, health insurance card, important way points, magnetic compass courses between known landmarks, and emergency phone numbers. Also print maps, charts, etc.
Always have duct tape on hand.
Use di-electric grease (tune up grease available at auto stores) on all electrical contacts, especially those that may become exposed to salt. I use it on my batteries, spare batteries, charging contacts, and gps upload link cord contacts.
Water bottles easily tolerate being deep frozen. Play things right and you may be able to have the luxury of cold drinks for 1-3 days.
A small package of damp face wipes is a nice luxury. A freshly cleaned face can provide "that just showered feeling."
Keep a leash on your visor hat. A lost visor, days from the store, would be bad.
Wear foot protection. A barnacle cut or a glass cut on the sole of your foot could ruin a good time.
Bring a mosquito face/head net. Wear it over your hat so the visor keeps the net off of your face.
Carry along a log book and make entries at least once a day. You'll remember this experience for the rest of your life and will take great joy in reliving it each time to think about it. You will remember a multitude additional measure of moments that occurred during the trip if you have notes that were made when the thoughts and memories are fresh in your mind.
Make this event an expedition. Think of the event as the entire expedition, not just as a 4-day trip. A large part of the experience is this, the planing portion. The gearing up and the gearing back down to return to the busy society is part of the expedition. All of the expedition is deserving of your full attention and will reward you with many memories.
GARY