I don't have a clue as to what this is referring to.

Horror/thriller movies

Maybe movies based on old board games?

My mind went straight to Rocky Horror Picture Show

I live on a ~90 hectare island with 4 residents scattered about and spotty signal (especially during heavy rains or thunderstorms).

I might not be the house servant, but it is fun when guests come asking about bad/no signal and you just sit there: "Oh yeah, that happens during bad weather, any problems? :) ".

There's also a running joke among my friends that you need to bring a "companion" if you want to be initialized... For undisclosed reasons. Also, don't feed the islanders, and don't let the campfire burn out if staying in the shelter.

What about the owner, when they inform the guests that there have been no servants in 100 years.

There's so many to choose from!

Or the guests, when they inform the owner that they know, because they've visited for 150 years.

The Shining

IIRC, the Torrance family were the only ones (living) left in the hotel when the snows came and they were being paid to be there.

Everybody gangsta until the fireplace starts speaking and the Manor informs all present that it wasn't even built until 89 years ago.