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.
Heading back to Lake Ontario for this summer. Now in Bermuda and heading to Long Island Sound in the first week in May. Then on to the Hudson and the Erie Canal.