Chuck, I have only done one offshore passage before and that was in 92. I had been working on a refinery construction project for a few years and the project was winding up. I was working for a company that did non destructive testing and my manager, who had been a recreational sailer for years had to take his sailboat back to Port Elizabeth to be hauled out and pit up on the hard while he went back to the UK to re-take his certification tests.
He had just gotten married, he must have been about 60, his wife early 30' s and several months into a pregnancy. It was supposed to be a routine trip of a bit more than 300 miles 2-3 days but after just a few hours out the harbor we were becalmed, then a swell started coming through and building. He looked at me and said " last time I saw these conditions, we were hit by a storm that nearly cost me the boat"
When the gust front arrived it was so fierce that within an hour visibility was close to zero, despite it being nearly mid day. We ended up running before the storm, bare poles and motor, into Plettenburg bay, where we tried to find shelter behind Robberg Penninsula. All done with GPS since it was black as night and salt water flying horizontally. The wind built up overnight to about 110mph with gusts to 130. These conditions persisted for 4 days. South Westerly gale was blowing opposite to the ocean current resulting in near vertical waves 40-50 feet high moving at 50mph. Many large vessels lost lifeboats off the back of their bridge 5 stories up due to those waves.
Our ground tackle held for 3 days and 3 nights and we worked to manage chafe, but on the 4th night we had some of the strongest gusts and started dragging the anchor and at last light the anchor rode chafed through. The skipper had a second anchor down, but not paid out and as he got the engine started and motored back closer to the beach, the second anchor chain fouled the prop. Transmission was destroyed and rudder was jammed and we lost propulsion and steering and started drifting down the cliff face of the peninsula towards open water and a huge submerged rock where previously mentioned swells were breaking.
We were goners till a group of squid fishermen, who use steel catamarans with diesel inboards responded to our distress calls. They got a line to us and pulled us away from whale rock with only a few minutes to spare. The tow back to the beach went on the rest of the night, it also co-incided with the storm finally abating. At about 6am they set one of their spare anchors and we were safe again..
One of my uncles was involved in offshore racing on that coast for many years and they had many close calls, but racing is not my cup of tea... They finally slipped out of the harbor one night and sailed across the atlantic to make a new life for themselves first in the Bahamas and later in Virginia....
You will want yourself and at least two other crew members for this long of a voyage. Four people on board would be better.
If you have never done a long passage on a boat you might want to hitch a ride with somebody. Lots of boats get delivered from the east coast down to the Caribbean in the fall and back again in the spring. You may not like passage making. Better to find out before you start building your boat if passage making is your cup of tea.
Lots of decisions to make.