Reimian Empire

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It is quite obvious that the phrases on the obelisk are part of a puzzle, which is also related to the numbered objects. As I see it, the pairs are as follows:

Pair 1:

1 — a creepy-looking chair equipped with handcuffs to fix the seated person's position. Next to it was a table with something that looked like a helmet made partially of wood and partially of iron. The unpleasant, sharp things intended for the ears, nostrils, and mouth were striking. The space for the eyes was covered with black and rough fabric. A flexible tube extended from the "top" of the helmet, going somewhere into the wall.

Brightwin
Sweet memories turn into nightmares

I have no idea what the solution might be here. Unless it's just a hint about what test awaits. Or what penalty there will be. If it's a test, I would recommend a character with high willpower. If it's a penalty, then someone who doesn't have pleasant memories.)))

Pair 2:

2 — a wooden table with an image of a raven in the center, with a human skull on one side and a crooked, rusty knife on the other.

Larian
The dead crave to see the light

I've already written a possible solution, but it could easily be a trick. It's just too obvious. However, if it purely determines the penalties, then the option with this solution is possible. Whether to risk it or not is up to you. Perhaps the puzzle can also be solved by creating a mask from the skull, which someone will wear. But I'm not sure what the consequences (if any) will be of such treatment of the skull. At your own risk, in short.

Pair 3:

3 — a sculpture of a dragon with its mouth open.

Laithia
A wise man never shares his experience

This pair arose purely by the method of elimination. It is possible that the phrase refers to object 1 (and its phrase refers to this one). I have no ideas on how to solve this. Don't put a head in the dragon's mouth?))) Unless, put the skull in there. But again, I can't guarantee anything. If it's about a penalty, then it's better to send someone with low wisdom and/or intelligence.

Pair 4

4 — a statue of a person in expensive clothes and a crown on his head, with a place for placing palms in the floor beneath it.

Darkiria
Kings demand the most important thing

Another obvious pair. As I see it, this is also about a penalty. The character will either lose some important skills, or the highest stat will be reduced. Or the result may be an injury (psychological or physical). In short, send someone you don't care about.)))

My useless insight ends here, solve the puzzle yourself. I am always happy to share a number of bad advice and incorrect solutions.

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Reimian Empire