With my first pirate, getting to Cuba the first time was a challenge, but really, isn't the game supposed to be challenging?? I remember sailing my light sloop through all that stuff, fingers crossed, hoping not to get sunk... It was one of the best parts of the game, early on.
They do seem to be making everything easier. Has anyone done the tp to padres quest recently? I seem to remember with my first pirate that I had to get raiders for that one, which I could not do alone and had to get help with. When I did it with my second pirate, the raider part was gone., and I did the whole quest by myself, in about 3 minutes.
Umm, Disney? Some of us like challenges!