Worst ''mess'' I ever got myself into was on a Hobie 18. I got knocked down and unbenownest to me there was small 1/4" hole due to corrosion at the top of the mast. So while trying to right it the mast slowly filled with water and it turned turtle.
Ever try to right a turtled cat with full sails and a mast full of water while singlehanded? Trust me, it''s not something I recommended