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Is it a type of wailing that sounds like someone in torture? Or is it more like what a caterwauling charm from Harry Potter is like?
Tan'ia Sense Motive: 1d20 + 7 ⇒ (9) + 7 = 16
It is the sound of ultimate suffering.

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"If no one pick lock, Harrow pick door!!!" he yells as he starts to smash the barrier with his polearm.
str check: 1d20 + 4 ⇒ (13) + 4 = 17
str check: 1d20 + 4 ⇒ (5) + 4 = 9
str check: 1d20 + 4 ⇒ (15) + 4 = 19

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I'm sure who ever is in side there is feeling a lot less afraid now.

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Harrow picks the lock: BANG!
The wailing immediately stops.
Harrow picks the lock some more: BANG!
It becomes clear that the door is barricaded. There's weight on the other side keeping it shut.
Harrow picks the lock yet again: BANG!
And one final time: BANG!
From the other side of the door is a frightened yelp. "Go away you horrible things! Return my sister and leave us alone!" There's a twang of a bowstring. Crossbow: 1d20 + 6 ⇒ (8) + 6 = 14 And a crossbow bolt bounces harmlessly off of Harrow's chest.
The party can see this poor fellow holding a crossbow in severely shaking hands. From the raspy sound of his voice/breathing, this is the person who has been wailing. The wet streaks on his face indicate that he has been weeping. The circles under his eyes tell you that he hasn't slept in a long time.
"Oh, Dimira! Dimira, where are you!" And more weeping ensues.

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Girion steps forward so he can see the person, makes a snap evaluation/guess, and holds his longsword in the air. "Do not fear, citizen of Kassen! We are here to rescue you!" He tries to look friendly, to offset the worked-up half-orc in front of the door.
diplomacy: 1d20 + 7 ⇒ (5) + 7 = 12

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"Hey, you not hideous wailing monster. Or are you illusion? Why you make such awful noise?!?"
Intimidate: 1d20 + 5 ⇒ (4) + 5 = 9

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The intimidate check fails.
The heal check might take a while. This fellow is clearly upset, and he doesn't trust you enough to allow you to approach him without some sort of successful social check, first.
At the mention of Kassen, the strange man pauses for a moment and looks at Girion. It's clear he doesn't fully understand. His faculties are not what they should be. But, the Son of Aroden has his attention.

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Harrow no! Bad half-Orc! We use our inside voice when rescuing people. the gnome scolds the half-orc before turning to the frightened villager. What my other friend said is true, we are here to rescuer you. Now please tell us what happened. Lumnessa asks with a slow even voice.
Intimidate: 1d20 + 5 - 1 ⇒ (18) + 5 - 1 = 22 vs. Harrow
Aid Diplomacy: 1d20 + 6 ⇒ (13) + 6 = 19 w/ Aroden
Or maybe he should be aiding my roll!

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Regardless of who aids whom, the man visibly calms down a bit. (That's not saying much, given that he's been wailing nonstop for a very, very long time!)
"Oh! Oh, thank Erastil. Not the angry bones! Where's Dimira. The others. We were attacked 2 days ago. I wish I had more soft pillows. What have you done with Dimira?!? Oh, the angry bones aren't behind you, are they? Not the angry bones! No! NO! AAAAAA!!!!!!"
Berosius can tell that this guy has been hiding in here for 2 days or so. He doesn't know how to deal with undead, and he's scared out of his gourd.

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I'm a little confused on the logistics. He shot a crossbow through the door? Are we all in the same room now? Is the door open?
1) Harrow banged the door open.
2) Wailing man shot the crossbow through the now-open door.
3) You can be in the room if you wish.
4) The wailing man is probably not capable of stopping you.

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Arak tries to help calm the man down, "We have dealt with these angry bones, as you call them. They are no longer a threat to you. Did they take your sister, or was it some other beast?"
Arak offers him a soft pillow, motioning for him to sit on it. Arak takes another pillow and sits on it himself.
Diplomacy: 1d20 - 1 ⇒ (8) - 1 = 7

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Bummer on the diplomacy roll. :-( Giving you a circumstance bonus for offering the pillow.
Never having seen a nagaji before, the wailing man is a little wigged out by Arak's appearance. But he starts to calm down a bit and sits on a nice, soft pillow. One of you recognizes him as Roldare. He's from Kassen.
"We didn't mean no harm. When the young folk come to the Crypt for their right of passage, we haze them a bit." (Hence the pillow-cushioned pits.) "But everyone knows it's all in good fun." (Hence the townfolk's over-the-top send off.) "Six of us arrived here 3 days ago to set up. Two days ago those things attacked us. Killed everyone except for me and Dimira. They took her..." His eyes fill with tears of frustration, grief, and fear. "AAAAAA!!!!!!"

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Harrow clutches his pillow and glares at Lumnessa for a moment longer, then remains silent.

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Where did they take her? Why did they let you go?
Not sure what roll I can make here, maybe sense motive to see if he's legitimately wacked out or if he's trying to lay a trap for us.
Sense Motive: 1d20 + 7 ⇒ (19) + 7 = 26

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Where did they take her? Why did they let you go?
Not sure what roll I can make here, maybe sense motive to see if he's legitimately wacked out or if he's trying to lay a trap for us.
He's telling the truth. He doesn't know where they took her. They didn't so much "let him go." Rather, they failed to catch him since he was barricaded in this room.
He witnessed her being dragged off by the skeletons during the fight and he is convinced she is not dead. He believes that "the voice took her."

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You may consider this barricaded room a safe place to rest, recuperate, store loot, whatever. I would not stay here too many nights, since villagers may come looking for missing folks and encounter baddies.
Once he calms down, the wailing survivor tells you in barely intelligible bits and pieces:
1) His name is Roldare
2) "You need the shields and the keys!"
3) "You will need to go for a swim."
You can ask him more questions, but you will not get any firther useful information out of him. If you try, these will be his next answers:
A) "Why when the mice spin?"
B) "Seven Ballstrom units. Yes, there are seven of them."
C) "Well, sdjhfksbdnlduvbksd, of course!"
D) "AAAAAA!!!!!!"
What does the party want to do? Where does the party wish to go next? There are 2 unexplored hallways in this immediate area.

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Girion considers Roldare's words thoughtfully, snapping out of his reverie when the man screams again. "First, we should escort you to the exit, so that you can return to town and warn the others. We will continue on and find your sister, and put this evil to rest, whatever it is."
Girion takes Roldare by both shoulders and gives him a little shake, looking directly into his eyes. "Can you do that, Roldare? The town must be warned. I promise you this, my friend: we will find your sister, and bring her back to Kassen."
Diplomacy: 1d20 + 7 ⇒ (18) + 7 = 25
To the others: "We will have to search the entire complex - does anyone have a preference for which direction to start?"

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I like him! Lumnessa declares. Can we keep him!?!?

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Harrow looks darkly at the cowardly man.
"I don't think he want go back to town. Very dangerous alone. His crying attract monsters that eat him."
The half-orc scratches his head, then says "Go back to entrance. Very mean horse there. He not kill you, but he not let other stuff kill you. Then we help back to town when we done killing everything that move here. Oh...I mean everything that not cooperate, then we report that we kill it."

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How sinister! the Lumnessa adds cheerfully as they continue forward.

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FYI, Roldare will find his way back to room 3. There are a number of bedrolls here, a pair of bullseye lanterns with 4 flasks of oil, 5 days’ worth of rations, and two potions of cure light wounds that are labeled as “healing.”
Harrow leads the way to the next room. When he opens the door, he can see that this small chamber is mostly empty, save for the body of a villager sprawled in the center.
(Map updated.)

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We are going to need a lot more daisies. Lumnessas says saddly

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Harrow approaches the corpse cautiously.
"This sister we looking for?" he asks.
perception: 1d20 + 3 ⇒ (6) + 3 = 9

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Perched atop the corpse is a man-sized brown and yellow beetle, trying to push the corpse into the corner. When Harrow opens the door and speaks, the beetle seems very, very angry.
Berosius: 1d20 + 2 ⇒ (9) + 2 = 11
Girion: 1d20 + 2 ⇒ (7) + 2 = 9
Harrow: 1d20 + 1 ⇒ (18) + 1 = 19
Lumnessa: 1d20 + 2 ⇒ (3) + 2 = 5
Tan'ia: 1d20 + 1 ⇒ (20) + 1 = 21
Giant Beetle: 1d20 + 1 ⇒ (20) + 1 = 21
Sorted Initiatives:
Tan'ia
Giant Beetle
Harrow
Berosius
Girion
Arak
Lumnessa
With the exception of Harrow (because he specifically called himself out as being at the front of the marching order), please feel free to re-arrange yourselves behind the half-orc on the map.
Tan'ia, you're up first. Then the beetle. Then the rest of the party. There's no surprise round. This is round 1.

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"Giant insect! And a wounded villager! Girion yells back to alert the rest of the group.
On his turn, Girion will move up to the beetle and try to bull rush it off the corpse, charging if possible. I don't have Improved Bull Rush so it will get an AO on me.

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Fire Bolt: 1d20 + 2 ⇒ (20) + 2 = 22
That's a possible crit, you should roll to confirm!

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Tan'ia, that's a potential critical hit! Roll again to confirm! :)
Confident that his companions have the beetle under control, Arak takes a defensive posture and guards the rear.
Ready action: punch hostile creature that enters my threatened area.

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Tan'ia confirms! She does 7 HP of damage to the beetle.
The beetle, singed and smoking, goes after the cleric.
Bite: 1d20 + 4 ⇒ (16) + 4 = 20, Ouch!: 1d8 + 3 ⇒ (6) + 3 = 9 Sorry, Tan'ia!
The Zenj woman takes 9 HP of damage and falls down.
The rest of the party is up!
Sorted Initiatives:
Tan'ia (9 HP damage)
Giant Beetle (7 HP damage)
Harrow
Berosius
Girion
Arak
Lumnessa
This is round 1.

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Hearing the cleric cry out, Arak rethinks this approach and rushes forward punching the beetle in it's stupid...carapace!
1d20 + 3 ⇒ (8) + 3 = 11
1d6 ⇒ 3

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"Hey! Leave little tiny healer gurl alone!!!" Harrow yells as he moves to sunder the beetle.
MW nodachi attack: 1d20 + 7 ⇒ (5) + 7 = 12 for damage: 1d10 + 6 ⇒ (10) + 6 = 16

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The beetle does her best impression of Keanu Reeves and "Matrixes" out of the way of Arak's fist. Harrow then comes in with his nodachi attack. The beetle does a slo-mo backflip, pushes off the ceiling with her left antenna, and lands with wushu-style grace. That's one flexible carapce! :-)
Berosius, Girion, and Lumnessa are up! This is round 1.

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Oh No! Tan'ia hang in there! Lumnessa cries just before she tears another tiny hole in the fabric of space surounding the bug in the terrible black cold of the Void.
Black Motes
Damage: 1d4 ⇒ 3 DC 15 reflex negates