1 - I'm not sure running down the coast puts me much closer to civilization, and I'm pretty comfortable with the crossing.
2- Being a Pilot, planning is my thing. We have 130 Gal on board and usually average about 2 mpg. Puts us well within the 50% range reserve.
3- I should have mentioned VHF, we have an installed unit with a whip, and also a waterproof handheld in the emergency kit.
4 - Good call.
5 - Food and water is usually no problem, I keep the freshwater on the boat full, and have at least a case of bottles under the rear seat.
6 - I will have 2 other people on board that are more than able to operate and Navigate in case something were to happen to me, this is important.
7 - This will be a must, I honestly don't think I would have done that if it were not for the suggestion.
Thanks for all the info guys, I have found it very useful, and I hope this thread will be a resource for those wanting to make the trip in the future. I will definitely give a detailed report when we get home!