hope you don't mind, but i have another goof ball idea:
i wonder if a couple of youths on a N17 (with a special reefing main) could tough it out for a couple days of no sleep. Those boats can hit 19kts. plus.
I would think that they could rig the tiller and both riders could stand up paddle in order to be first to the wind line, or to deal with check points, extreme lulls, etc. The long paddles, if customized could be used to pole against the bottom as well.
or, if there is like a used Marstrom A class fairly cheap, and put spi., reef points, storage, etc. Then when you need to paddle to the wind line or whatever, you figure out a way to SUP. Maybe build a liteweight deck area for standing forward of the front beam.