Rubin, with the ropes set and in place, starts down into the hole.  Having lived in the underdark for several years now, he knows the danger of tremors and the likelihood of more of this section of tunnel falling in on the children.  He is moving quick to get down and start getting those kids out to safety.  He will go all the way down to where hte kids are.

Athletics check, if needed: 14 / if with advantage: 13

"You make it down there OK?" Jairus calls out to Rubin.  If he answers in the affirmative, he turns to the other allies, including the newcomer.  "Who's next?  I could go if ya like, but I reckon Kethra is the stronger climber."

Rubin and Damian, you see a wide, irregularly shaped cavern with a floor of smooth bedrock. Damp dirt and stone, with tree roots protruding here and there, make up the walls. A five-foot-wide tunnel leads off to the north, and a stone slab — a door with a rusty pull-ring — stands to the east. By the stone door, a couple well-used cloaks and a waterskin are on the floor.

There's a pile of dirt roughly in the middle of the room, where four shocked children and a woman are currently sitting (you're about 5 feet from them).  They look bruised and confused, but not majorly injured.

The children all shriek when a large cat lands next to them, but carefully start to crowd around it when it makes no aggressive movements.

Kethra, the elder you accost takes one look at you and storms off as well.

Symon steps up.

"I'll head down next."  They had people down there already, and there was no immediate danger to provide cover fire against.  Keeping his crossbow away from the rope itself, he descends into the sinkhole one-handed.  As Tyde said, there would be time for introductions later.

(Athletics: 10 if necessary.)

Symon makes it down without any issues.

"Let's start tieing the ropes so that someone above can haul the little ones out first."  Rubin suggests, heading over and nodding to the children.  "Who wants to be first for a fun ride back up?" 

One of the children approaches cautiously, and the woman quickly herds the others over.

"Go to the nice man with the rope, he'll help you get out of here."

(I thought I had posted, but I forgot! Sorry guys.)

A bit stunned from the Elder's rude exit, Kethra shakes her head upon hearing Mr. Tyde's friendlier voice. She approaches the hole to get a general idea, but not too close, her cloak billowing to the side from a gentle gust caused by the sudden cold air below meeting the warm, sun-baked air.

With the bravest voice she can muster, she calls out to the boys who have bravely taken initiative and jumped into action. "Mr. Tyde, please keep a lookout! Investigate that the rope is placed best so that when the kids climb out...the edge won't collapse on the people below! The guys will probably be waiting right under them to catch them if they fall...right guys!? Davian, Rubin and uh...Symon down below, please wait a moment!!"

Quote from Izraal1 >>

"You make it down there OK?" Jairus calls out to Rubin.  If he answers in the affirmative, he turns to the other allies, including the newcomer.  "Who's next?  I could go if ya like, but I reckon Kethra is the stronger climber."

"Jairus, I need a favour," she grips him on the shoulder as he's looking into the sinkhole and hands him her own bundle of rope. "I'm...not very confident I can keep them safe. I need your dexterity to tie us a hitch to something secure. That way the rope will tighten on itself if I accidentally let go while I try to pull them up. Then you re-adjust the hitch, then I continue pulling them up! Then they can use Mr. Tyde's rope to steady themselves as they climb."

If Jairus gets up to do so, she'll quietly add so that only Mr. Tyde and Jairus can hear, "Pass the globe to Mr. Tyde just in case any of those Delvers come out. I'm kind of scared to think of what they look like and what they might do, but they shouldn't be used to a bit of Daylight, right?"

Her voice cracks a bit at the end, then she takes a deep breath as she again calls to the people below.

"We're sending another rope down! Please secure the children to this rope!"

Kethra will then take the Ready to pull once the people below gives the all-clear.

Edit: a link

Following instructions, and having his own experience with these exact sorts of situations, Rubin gets one of the kids ready to be hauled out.  "Ready down here!" He calls up when the child is safely set to be hauled out.

Jairus listens carefully to Kethra's instructions, and immediately agrees with the plan, adding, "And this is why you'd be a darn good leader, Kethra, better'n me for sure," as he attempts to use his body to conceal passing the globe to Tyde - Sleight of Hand/Dex Check 17 - and immediately begins looking for some sturdy anchored object  or structure that would serve as the hitch for these purpose.  Jairus' outlander upbringing included a fair number of knots, and the occasion where transporting a carcass was needed, which required some 'light engineering,' but he has no formal training.  

Investigation:  24

Perception:   21

Dexterity Check for "Use Rope":   22

Symon does not attempt to assist the children in their ascent.  Too many bags spoiled the child soup, after all.  Instead he continued scanning the cavern for any sign of trouble.  His stance began to relax.  It was starting to look like they were in the clear.

Cat-Davian remains standing next to the waiting children. He purrs in hope to keep the children calm but in reality he is watching into the darkness of the cavern. He takes in big breaths through his delicate nostrils attempting to pick up any scent of danger.

Perception 19

The area Tyde points to as stable promptly collapses in on itself and falls down into the pit.

There's no sign of anyone else in the chamber, and there's no sound coming from behind the door or the passageway.

Jairus ties an exquisite knot, using a nearby post for leverage.  Are you going to try to hoist one of the children up?

(Note: for things like tying knots I usually count that as sleight of hand.)

Quote from LordShadowthorn >>

The area Tyde points to as stable promptly collapses in on itself and falls down into the pit.

There's no sign of anyone else in the chamber, and there's no sound coming from behind the door or the passageway.

Jairus ties an exquisite knot, using a nearby post for leverage.  Are you going to try to hoist one of the children up?

(Note: for things like tying knots I usually count that as sleight of hand.)

 Kethra has a Readied action to Hoist a Child up once the rope is tied off, actually - Jairus might Help her if possible, to grant Advantage, but she is the primary "puller."  

OOC: I was just doing it as a straight Dexterity check, also as a throwback to 3.0 D&D which had a Use Rope skill.  

Symon watches the dirt crumble as the group struggles to get the children back out of the sinkhole.  Eyeing the door reluctantly, he begins to stalk towards it.

"My friends, it seems the only way out is through."

Kethra pulls up a child (no check required).  Do you want to repeat the process for the other 4 civilians stuck down there?

Symon approaches the door.  Nothing odd happens.

Quote from Izraal1 >>

Kethra has a Readied action to Hoist a Child up once the rope is tied off, actually - Jairus might Help her if possible, to grant Advantage, but she is the primary "puller."

(Thanks!)

Quote from Brian_Avery >>

"Looks like it's not as a safe as I first thought." Glancing around at the others, "We should go down and help the others when they go through that door. It might be where those Delvers the mayor spoke of are keeping themselves."

Tyde will follow the 1st member of the party remaining above, if they climb down to join the others. (If someone suggests a better plan then he will follow that instead.)

"Rubin!? Is everyone alright?"

Panicking from seeing the ground collapse, Kethra nods nervously at Mr. Tyde's suggestion. 

"Jairus and I will lower you down first so you can get a closer look…I'm sorry for putting this pressure on you, Mr. Tyde. But thank you."

"Everyone down there, stay clear of the edges! Please!"

Quote from LordShadowthorn >>

Kethra pulls up a child (no check required).  Do you want to repeat the process for the other 4 civilians stuck down there?

Symon approaches the door.  Nothing odd happens.

 OOC: I can’t speak for another player but if it worked for getting one child up I would assume we would work together to repeat it until they are all rescued. Jairus would aid with the process. 

(tyty for pointing that out! I didn't notice that the DM posted 2 minutes right after I did. Yes, I totally will do that with Jairus if that's allowed.)