I bet the South Wind would be fast with the Hobie sail though.
I could add a keel with a heavy lead weight on the bottom.

. . . .
Get a grip there, Jimmy!
Almost too funny!
Now I'm a laid-back, take-t-easy and enjoy the trip, cruising sailor, but I also looked at it a bit differently in the past.
Used to have a little 13 footer (one foot of that was a beautiful wooden bow sprit,) that carried a mast and set of sails for a 18 foot one-design class boat. That little thing would plane on a heart-beat. (It also taught me the meaning of the phrase, "knock-down."
Later on, I crossed a yard on the mast and flew a home-made square main with a raffee (topsail) above it. This was able to drive the boat up onto a plane, dead down wind when it blew hard enough. I once spent 8 days cruising the Gulf of Mexico in that boat, including sailing her right up the Egmont Channel, under the Sunshine SkyWay's center span, into Tampa Bay. Strictly white-knuckle sailing.
These days, I'm looking for a sailing rig as an alternative propulsion system, one that I'll enjoy using. Just another method of getting around on the water in an enjoyable, relaxing fashion.
So, for the South Wind and the Freedom, that will mean a sail with only 30 to 40 sq. feet. Rather than Tyvek, I may go with some easier to work with material from one of the kit making supply shops. I've messed with that before and some of their ripstop nylon materials are strong enough, very light, easy to work with, and comes in just about any color (or pattern) you'd want.
Mike S.
Spring Hill, FL