On your "hardest puzzle" for LSL2:
Spoiler:You are always told what the reason is for the soldiers not believing that you are a woman. If you haven't stuffed the bra, they say you are flat-chested, so the solution becomes obvious.
Incidentally, I would call all the trial-and-errors related to that puzzle "dead ends" (although it's been 8 years or so since I played it), but maybe you're considering them "deaths"? Same with the deaths on the lifeboat.
Very inspiring thread. I might have to start one for games that are new to me as well.