DAY 5:
I fixed the issue with the keys — now they spawn randomly in the dungeon, with only three in existence tops at any time. On top of that I started to design the jailer A.I, modeled with a state machine. Basically, there are different "states" that the A.I can have, and its behavior has to model that.
Where α is whenever the player (1) finds a key (2) runs around for a while or (3) when all keys are found, which is kind of a special case where the A.I will never patrol or flee. β is the funny situation for when the jailer is blinded when on patrol. This might be overkill, but it does help me at least visualize how to code this up. I also don't have experience drawing a state machine, so there's that. Didn't do a whole lot but daydream.