Mike,
It looks like you have successfully understood my comment/question about a discuss or triangular shaped bobber that would be relatively flat. I see two problems, besides the obvious problem of building a thin and wide float that would withstand the impact force of a violent pitch pole roll.
1) Winglets are usually located near the leech, rather than the luff.
2) A agree with David L. in that they are not for everyone. I for one, will stick with a mast that can be intentionally buried for survival at sea in heavy wind.
To take of #1, I would consider a teardrop shape that would span the entire chord of the square top sail.
To take care of #2: If I decide to add buoyancy up there, I'll go with the smallest, cheapest West Marine inflatable vest. It is an easy project. That vest is contained in its own waist pack that can easily be riveted to the mast and a pull string lead down to the dolphin striker.
But honestly, I keep my mast sealed enough to endure a turtle experience. And if I have to stay turtled for an extended period of time, I won't count on being able to right the boat again. Why? Because I wont' count on my mast not having a very small leak that would eventually fill it up if left turtled for hours. After that, I don't think that an inflated horseshoe vest would be enough buoyancy to lift the mast and sails to the surface.
GARY