Re: If I had to get one new sail, what would it be?
I agree on Bacon Sails. They are quite conservative with their condition descriptions. Any sails rated 'good' or better will meet your needs and you should be able to get a genoa and working jib for the price of one new sail.
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.