OOC: It didn't end up mattering with the dagger's attack roll, but rapiers don't have the "light" property, so bonus attacks with a second weapon can't be taken after a rapier attack.

Also, unfortunately, in 5E you can't move through the space of an enemy unless they're 2 sizes larger than you. Not that you would end up wanting to here, as you'll see. Poor Bob would go crashing through the chimney to the floor below.

Entirely focused on Tarok, Klarg suddenly feels Bob's rapier blade quite painfully in a lower region, a new wound now dripping blood. Argos remains in unconsciousness at the entrance to the cavern.

Turn 2 Remaining:
Sildar <===

As he rushes into the cavern, Sildar takes quick stock of the situation and charges toward the only available target, the sleeping goblin.

Scimitar Attack: 18
Scimitar Attack: 5

With impressive speed, Sildar slashes twice across the goblin's chest with the scimitar he had pilfered earlier, dealing 8 and 9 slashing damage, ending the goblin in its sleep.

Turn 3 Remaining:
Klarg <===
Players
Sildar

Once again disengaging to escape the terrifying half-orc chasing him, Klarg quickly attempts to scale the chimney below him.

Klarg Athletics: 4

As he descends he meekly shouts upwards "Klarg come back, then Klarg make a throne from your puny bones" 

Turn 3 Remaining:
Players <===
Sildar

Tracking:
Klarg, carrying two large wounds, is scaling down the chimney, halfway down the 30 foot distance.
Tarok and Bob are at the top of the chimney.
Nemean and Sildar are 30 feet from the chimney, near the supplies and goblin corpses.
Argos is unconscious at the cavern entrance next to Cinis, 20 feet from the chimney.

Bob is going to jump down on to Klarg rapier pointed first. 

Attack-15

Damage-10

Dex save -7

Just before Bob takes the plunge down the chimney, Cinis runs to the top and unleashes a final  Fire Bolt at the fleeing bugbear with a hissed "Sruthan" and a hurling motion with his hands.

Attack: Unable to parse dice roll.

Damage: Unable to parse dice roll.

(OOC: Trying the rolls again. )

Attack: 21

Damage: 4

OOC: Wow, what a move!

DM Screen:

Bob launches himself down the chimney with a sudden unexpected ferocity. Rapier pointed down, his aim is thrown off just enough as Cinis launches a fire bolt that strikes Klarg in the back. Bob lands on Klarg with a thud, and they both fall from the chimney in a smoking heap, each taking 5 bludgeoning damage.

 They now lie prone in the room with the wolves, on the opposite side of where you had entered earlier. Upon seeing the tumble, the wolves begin snapping and snarling, unable to reach the intruder while tied to the rods that hold them near the room's entrance.

Initiative:
Wolf 1: 8
Wolf 2: 8
Wolf 3: 3 (-5 for nat 1)
Average: 4.6667

 Turn 3 Remaining:
Argos (unconscious), Nemean and Tarok <===
Sildar

Tracking:Bob and Klarg are laying prone at the bottom of the chimney.
The wolves are 20 feet from Bob and Klarg, tied to rods at the base of a stalagmite.

OOC: Descending the chimney requires a Strength (Athletics) check. A success means you can move at half speed down the 30 foot chimney.

Tarok stows his sword and climbs down toward the others.

Athletics: 21

Tarok easily finds handholds in the natural chimney, climbing halfway down.

Turn 3 Remaining:
Argos (unconscious) and Nemean <===
Sildar

OOC: I’m sorry guys very hectic day at work, and won’t be able to do a proper post til much later.

My intention is for Nemean to hustle down and attack Klarg with both scimitars asap. I think between feline agility and the tabaxi climb speed I can make it in one move. 

I will edit this for roleplaying purposes, and use the dice roller, but didn’t want to hold up everyone else since you’re waiting on me. 

Update:

Nemean stows his scimitars, and for a brief moment holds himself perfectly still.

“This stinking Klarg thinks he can escape from Nemean Golden? I can catch him! Nobody is quicker, nobody is a better climber, certainly not this this Klarg. Perhaps he is more bug than bear after all!”

A twitch from his tail precedes him boldly surging forward, and wildly leaping down the chimney...

OOC: I told you I could make it down there in one move... I imagine something like this

OOC: Thanks, that's appreciated. From 30 feet away from the chimney, Nemean would at best be able to stow his scimitars and make it to where Tarok is halfway down (30 feet movement + 30 feet for movement halfway down chimney).

Nemean Athletics: 4

 OOC: Eep, nevermind, you got down the chimney.

 Claws launching him forward, Nemean blazes across the cavern, jumping into the chimney just before Tarok begins his downward climb. However, his velocity carries him through too fast, making it difficult to slow his descent. Unable to grab a foothold in time, he crashes to the floor below, taking 15 bludgeoning damage, knocking himself unconscious as Bob and Klarg are pulling themselves up.

Turn 3 Remaining:
Sildar <===

Sildar, still badly damaged, shouts to Cinis. "Go after him! I'll ensure nothing happens to Argos!" He runs over to where the dwarf lies unconscious and stands protectively nearby.

Turn 4 Order:
Klarg <===
Players
Sildar
Wolves

Klarg now looks truly terrified of these intruders that are now literally throwing themselves at him. "Maybe Klarg not come back, maybe you keep cave, that fine!" He shouts and dashes out of the room, darting left toward the cave entrance, not taking so much as a glance backward to see if Bob and Nemean are getting up.

Turn 4 Order:
Klarg
Players <=====
Sildar
Wolves

Tracking:
Argos is unconscious in Klarg's room with Sildar.
Bob is prone at the bottom of the chimney, 20 feet away from the wolves.
Nemean is unconscious and dying at the bottom of the chimney.
Tarok is halfway down the chimney. (One more successful Strength (Athletics) check will allow him to reach the bottom safely)
Cinis is at the top of the chimney.
Klarg is out of sight, last seen turning left out of the room toward the cave entrance.

(Wouldn't Klarg also need to use half of his movement standing up from being prone? So he shouldn't be out of sight, right?)

OOC: For clarity's sake, the room is 30 feet long. He used the Dash action, so he had 15 feet of movement + 30 feet of movement from dashing. If you'd like, I can start including summaries of enemy movement if the descriptions aren't clear enough.

Tarok tries to climb down and chase as quickly as possible.

OOC: There isn't a double move in 5E?

Athletics: 21

(Makes sense. I forgot about Dash.)

Cinis grumbles to himself and attempts the chimney. 

Athletics: 19

"Hm. This is actually a lot easier than I thought." He says quietly to himself as he makes his way down.

OOC: In 5E they just replaced "double move" with a specific action called "Dash" that doubles your movement. I don't think there's any difference in their function, just the name change. Tarok could use that at the bottom of the chimney if you'd like to add that on, but you can't use Disengage as an action in the same turn, so you'd be open to attacks of opportunity from the wolves.

Tarok reaches the bottom of the chimney, landing softly next to the prone Bob and Nemean as Cinis begins his descent, easily finding footholds and moving halfway to the floor below.

Turn 4 Order:
Klarg
Players <===== Argos (unconscious), Bob, and Nemean (dying) are up.
Sildar
Wolves

OOC: No worries, seems like it's impossible to catch him now.

Quote from Smullzilla >>

OOC: I told you I could make it down there in one move... I imagine something like this

 Bob is going to stand up and mutter to him self. And then go and stabilize Nemean with a kit.

DM Screen:

Turn 4 Order:
Klarg
Players
Sildar <====
Wolves

Sildar drags Argos to a safer spot in the chamber and continues to stand guard.

Turn 4 Order:
Klarg
Players
Sildar
Wolves <====

The wolves have worked themselves into a frenzy, throwing themselves to the ends of their chains and snapping their jaws. 

Tracking:
Argos and Sildar are in Klarg's chamber. Argos is unconscious.
Bob, Nemean and Tarok are at the bottom of the chimney. Nemean is unconscious but has been stabilized.
Cinis is halfway down the chimney. (One more successful Strength (Athletics) check will allow him to reach the bottom safely)
Klarg is out of sight, last seen turning left out of the room towards the cave's exit.
The wolves are 20 feet from the bottom of the chimney, unable to move away from the chains tying them to rods at the room's entrance.

Turn 5 Order:
Klarg
Players <===== in any order
Sildar
Wolves

Athletics: 4

Cinis clumsily continued his descent down the shaft. The time it took to get down was really putting a strain on his muscles. He made it to the bottom and saw the wolves pulling at their stakes. He immediately recoiled when he saw the bloodthirsty animals, but steeled himself when he saw they were chained. He looked over at he unconscious Nemean made up his mind.

Those chains don't look like they'll hold forever. I hate myself a bit for this, but it has to be done.

Cinis reared his hand back and threw it forward, softly saying "Sruthan" as he did so, tossing a Fire Bolt at the wolf that looked the closest to escaping.

Attack: 17   Damage: 6

(Forgot I probably get advantage because they're tied up. 15  )

Tarok tears off after the Bugbear as fast as he can, hopefully following the blood toward his quarry.

OOC: Can I do a move/dash or something else to try to close the gap?