First off, I want to say that I've never played Wind Waker in my life until the other day. I am currently playing through the remake of the game open minded, so I must figure out each and every challenge that comes my way.
With that said, my first real challenge for me was when I reached Windfall Island, and to be quite truthful: I was kind of PO'ed when I was taken from the Forsaken Fortress by that dumb bird. At Windfall Island I wandered in circles, unable to figure out where I was supposed to go in order to find a sail. After what seemed to tally up to 6 HOURS (I know...) I finally managed to get a sail by first freeing Tingle and then finding a pictobox. I was so happy (as anyone would be) when I finally got the sail. So happy to the point where I decided to do some of the side quests on the island before departing.
My next obstacle was the Dragon Roost Cavern Boss Battle. Apparently, this boss battle was problematic for a lot of people, which is understandable because your first guess wouldn't be to look up at the ceiling when you enter the boss room; you're more concerned with the giant scorpion-like monster in front of you than with a Dragon tail sticking out from the ceiling.
Game over, after game over -- my frustration was growing. I then had to look up how to defeat the boss. I was at relief once I defeated him.
(Wherever I get stuck next I will add on to this blog)
The Legend of Zelda: The Wind Waker HD: My Struggles
Frustration at its finest...