If sailor takes all precaution and goes over safety precedures for every possible scenario over the next week and brings basically the safety equipment like harnesses and brings life raft and food and water supply, water purifier, a good main sail and a back-up mainsail and a storm sail, a gps unit with computer tracking, maps/ charts of the whole West coast. I have some seatime I was working on a fishing boat and doing nightwatch on it.
For sailng, although I read about it, I might take a few lessons. Tighten the rigging, two new batteries (one deep-cycle). I have a sextant and books. I want to head south and stop at every town with the idea of doing it in one season.
Reading about it isn't the same as doing it. You need to know it well enough that when the nasty weather sets in or a problem occurs, you can deal with it without hesitation. Most problems only get worse if there is a delay in dealing or resolving them.
What would you advise as far as weather openings.
Depends on how far you're planning on going in a single leg... the longer the intended distance, the narrower the window will be.
Rather than just saying we should not do it, what would a plan for this trip look like as far as optimal time to go and where to stop.
Has anyone done such a journey?
Again, this depends a lot on the boat, the captain, the crew, the weather, the time of year, etc. Yes, it has been done before. Yes, people have also died trying it.
How much more unsafe is the ocean compared to a freeway in NYC in an old car in good shape?
The ocean is probably safer, but in many ways less forgiving. If your car breaks down, you won't drown or sink... If your boat has a problem, you very well may. If nothing goes wrong, the ocean is safer... but if you make a mistake, the mistake is far more likely to kill you. For instance, if you fall off the boat and the remaining crew isn't skilled enough to get back to you and recover a MOB....you're likely dead.