Okay, so I should have mentioned this is a low polygon count image. Most of what I’m learning now is low polygon stuff. The Decimate Modifier, therefore, was used to lessen the amount of faces the image have.
Down to around 1% of the number I had.
Having a better idea of where I wanted the project to go, I fiddled about after I decimated (kinda) my island. The result is closer to where I want to end up.
To illustrate, before:

After:

While I’m partial to Before, this will make it easier for me to reach my final goal.