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.
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.