i have had to do the swimming at the bow thing to get the boat in the right orientation. The boat really doesn't want to get in the right position unless you do it because the mast and sail act as an anchor for the tramp so it wind vanes like that. It can be worse though if the mast is downwind because then it wants to make the boat turtle
if you can put the mast under the water and find the leaks then just smear the crap out of them with 5200. I did that a couple years ago where the diamonds go into the mast.