most painful had to be during my first play through. i had just completed my iron set, had my swamp key, my wishbone, my frostner. and decided to take the longboat and see if i could find the base of that giant tree in the sky. found the edge of the world. thought "oh thats neat." went to turn around, and the current pulled me off the edge. wind was blowing in my favor and everything. lost all my gear + a longship, and you cant sail over the edge again just to grab your stuff. its gone...