3). A safety-line under the tramp is important, and would have given me something to properly hold on to while sorting out the steering gear.
4). I just spent $55 on a 28" wide sea anchor which I believe will prevent or reduce the drift rate to a speed that is swimable as It should also hold the bow to wind eliminating windage on the tramp.

Being fit enough to swim the distance you choose to sail offshore is probably a good guide to how fit you should be, or how far offshore you should go.