I tested the Pirate Caverns. The result is looking interesting, I just have a few adjustments to make.

There will be checkpoints in the Pirate Caverns (if you die you will return to where you left off), HOWEVER, if you quit the game you will have to play night 3 from the beginning. I'm going to put this system in place because otherwise it would take 3 hours at each checkpoint and the night would be much easier, so no.