Actual Sailing and Discovery were two "pillars" I had in my mind, so I'm glad you picked up on that and had a good time out on the water. Good critique points here. I was aware that the against the wind sailing also featured that difficult camera angle, but I sort of thought it seemed appropriate for sailing close-hauled like that. Besides, also throwing in camera rotation on top of boat rotation AND sail rotation and keeping track of the wind, I thought it was probably doomed to be totally overwhelming for jam players, probably riding the edge of that as it is.
Your first impression was the correct one, there are some shortcuts in the level, but you have to get the wave timing just right to clear them (hint: backwind your sails to slow down), it's not easy but can shave serious time if you master it. And on the last point, I think I agree. I did it that way to prevent the player from getting stuck when running aground and because it makes me laugh, but I think it is indeed probably a bit overdone with a few days hindsight now. Thanks for the in-depth look. I just had a look at your game too, I'll leave my review over there :)