Bearrik storms forward, partly climbing on the wall to avoid smashing Bleep as he goes. Ghee does not have a wall next to him for support, so when the large bear comes rushing, he does his best to balance on the edge of the stone bridge:

-> Ghee's DEX saving throw {DC 14}: 21 

Ghee does just enough to avoid falling into the lake deep below. 

Bleep takes advantage of the furry distraction and shoots a bolt at the one enemy he can see from his spot. Unfortunately for the grung, that's the one enemy carrying a shield, and his bolt ricochets away from it. 

(Ghee's turn is still up.) 

Following his own near drop into the water below, Ghee reasons it would be a shame if something similar were to happen to their attackers.

Moving forward to just behind Bearrik, he removes the stopper from his decanter and aims it towards Tooth. Speaking it's command word, Ghee unleashes a torrent of water from underneath the brown bear in front of him, hoping to knock them off balance and into the pool of water below.

(OOC Slight re-flavouring of the decanter's powers. Tooth needs to make a DC13 strength save or be knocked prone, taking 1d4 damage in the process. I'm just hoping to try and up the fall damage given that there's 30 gallons of water heading their way.)

DM's Screen:

(@MB: There's some loose interpretation of the "Geyser" option of the Decanter of Endless Water going on, but let's roll with it. Nice creative thinking!)

Ghee steps just behind the brown bear {N-45} and screams out: "Geyser!" while uncorking his magical decanter. Thirty gallons of water shoot out of the item with such force that Ghee has some trouble controlling the jet. Most of the water simply travels past the target and into the abyss, and whatever amount hits the lizardfolk is diverted harmlessly by his shield.

(Cat Keeper and Toothless go next.) 

Cat Keeper looks at Bearrik with eyes that say: "A worthy opponent." She unsheathes a large two-handed greataxe from her back and brings it down on the bear, before slicing back upward.

-> Greataxe vs. Bearrik: Attack: 10 Damage: 12  

-> Greataxe vs. Bearrik: Attack: 16 Damage: 7  

She seems a bit too eager at first, hitting only the ground. However, her upward slash catches the bear's belly. (Bearrik takes 3 slashing damage, already halved.) 

Toothless wraps his hands around what looks like an oversized meat hook and tries to sink it into the large bear in front of him:

-> Hook vs. Bearrik: Attack: 17 Damage: 4  

It goes in deep, and Bearrik lets out a roar of pain. (Bearrik takes 5 piercing damage, already halved.)

-> Bearrik is now grappled.

(Ang is up next.)

With a better view of what is coming up, Ang comes back onto the bridge (R44) and runs towards the group of enemies (N44, cunning action) but not in close melee.
Then, instead of using her crossbow, Ang takes her Whistle-stick of Haunting and starts playing a deep melancholic tune. Magically, this tune seems to be heard only by her foes.

(DC 15 Wisdom saving throw or become frightened of you for 1 minute)

DM's Screen:

Ang hops back on the overpass and swings her magical whistle-stick repeatedly. She can see the eerie tune resonates with the lizardfolk and the goliath, but the half-orc and the human do not fall to its spell.

-> Tooth and Cat Keeper are now frightened. 

(Tooth goes next.)

The bear being the most obvious threat, Tooth attacks ferociously:

-> Heavy Club vs. Bearrik: Attack: 14 Damage: 6  

-> Bite vs. Bearrik: Attack: 21 Damage: 8  

The lizardman bonks the bear on the head but, with fear in his eyes, he retracts his attempt at biting the beast. (Bearrik takes 2 bludgeoning damage, already halved.) 

DM's Screen:

END OF INITITATIVE ROUND 2     

GANG FIGHT - INITIATIVE ROUND 3

• 20. Khan (47/48) - 80 ft. away from {X-45}, movement halved (20ft.);
• 18. Dwarven Miners - 
• 16. Saros & Omen (32/32) - Omen is ready to help;
• 16. Gregor Forskog (red) - 
• 16. Darrik (56+24/56+34) - Rage, grappled, in the form of a Brown Bear;
• 13. Bleep (38/38) - exhaustion;
• 10. Ghee (41/63) - exhaustion;
• 10. Cat Keeper (blue) - frightened;
• 08. Toothless (black) - 
• 06. Ang (27/38) - exhaustion;
• 03. Tooth (green) - frightened;

MAP:

 

NOTES: Notable enemies have been color-coded. Variant "Hitting Cover" rule applies, though I will no longer post cover reminders in the initiative tracker above as it depends on the angle of the incoming attack.

(Khan is up next. As requested, I'll assume she simply keeps moving forward this turn.) 

Khan and Blip continue to get closer to combat as their speed permits.

Not having a clear shot at Ghee anymore, the miners decide to aim for the easier target around: 

-> Light Crossbow vs. Bearrik: Attack: 6 Damage: 2  

-> Light Crossbow vs. Bearrik: Attack: 15 Damage: 5  

-> Light Crossbow vs. Bearrik: Attack: 13 Damage: 7  

-> Light Crossbow vs. Bearrik: Attack: 10 Damage: 9  

All four bolts hit their mark. (Bearrik take 8 piercing damage, already halved.) 

(Saros is up next.) 

Saros weighs up the scene before him and holds off on any more major spells for now, choosing to step forward 10ft (within 60ft of Gregor) and he will call to Omen to Help and targeting him with Ice Knife, flicking a drop of water toward him and drawing the magic into it, the droplet becomes a shard of ice that flies toward the attackers

Attack 24 Damage: 10  (rolling with Adv assuming Omen can Help)

Whether or not the shard damages Gregor, it explodes and Gregor and those within 5ft must make a DEX 15 saving throw or take 9 cold damage

Saros will then retreat back into the cover, taking a moment to peer back down the tunnel, a little concerned that Weirding and the others must know where the party went, and may seek to close from behind.  As soon as Khan catches up, he will make this observation to the Grung to see whether she agrees.

(Bearrik isn't within that 5 feet, correct?  That's what it looks like on the map.)

(Also, this is faintly ridiculous.  I've been hit like 7 times and bearly lost half of my health.)

(Posting my turn early for convenience.  I'll spoiler it so it's not too confusing.)

Quote from LordShadowthorn >>

(Bearrik isn't within that 5 feet, correct?  That's what it looks like on the map.)

(Also, this is faintly ridiculous.  I've been hit like 7 times and bearly lost half of my health.)

Gregor is the Red one at the back of the Group per the last map (J45) (at least that is what I was intending to hit)

DM's Screen:

(OOC: Bearrik doesn't need to roll a saving throw, but Omen does.)

Saros steps out of his nook intending to hit Gregor with his next spell but, with so many warriors between him and his target, the wizard asks his familiar for some help aiming the spell. Omen flies in a curve, reaching the other side of the melee happening at the overpass {I-44}. From there, he files around in small figure-eights to indicate Gregor's exact position. That's when Saros finishes forming his icy shard and launches it in an arc.

The whole effort pays off. The shard is quite accurate, hitting the half-orc's throat and sinking in deeply before exploding. Gregor struggles to breath and stumbles around for a couple of seconds, but never manages to solve his predicament. (Gregor takes 8 piercing damage and is DEFEATED.)

-> Omen's DEX saving throw {DC 15}: 9 

The many resulting ice shards then pierce Cat Keeper's and Toothless' backs, but the female goliath seems little bothered by the magical cold. Tooth's trusty shield proves to be useful once again, blocking all tiny shards and dust flying his way. (Cat Keeper takes 2 cold damage; Toothless takes 4 cold damage.) 

Once the icy dust clears, Saros notices that Omen is nowhere to be seen. He puts two and two together. (Omen takes 4 cold damage and PUFFS OUT.)

(Gregor is dead so we'll go straight to Bearrik's turn.)

(@Shadow: The most visually injured enemy in front of you is the lizardfolk.)

Finally having a chance to retaliate, Bearrik picks his first foe and attacks savagely. His fangs meet Tooth's shield, but the claws strike flesh. Long, deep gashes are left on the lizardman's left tight. (Tooth takes 11 slashing damage.)

Before attacking again, Bearrik forces some of his puncture wounds to begin magically closing. (Bearrik heals for 6 HP.)

(Bleep and Ghee are up next.) 

Not fancying the climb and potential drop off into the murky water that would be necessary to bring himself into hand to hand combat with this in front of Bearrik, Ghee drops to his belly and pulls his blowgun from his pack.

Normally reserved for stealthier encounters and normally used to deliver poisons and venoms to his foes, Ghee hopes his caltrops back at the entrance of the tunnel are doing good work to any looking to sneak up on the party.

Taking aim between bear legs in front of him, Ghee lets a dart fly at Toothless.

Attack - 18

Damage - 4

Keeping where he is, Bleep sends another bolt at Toothless.

Light crossbow (adding sneak attack): Attack: 21 Damage: 15

(@MB: I'm afraid that by going prone, you inflict disadvantage on your own attacks. Here's a second roll: 9.)

Bleep's direct line of sight to the only human on the bridge is very narrow, but the green grung nonetheless attempts a shot. HIs insistence pay off, with his latest bolt finding its target and going through his studded leather armor. (Toothless takes 15 piercing damage.)

Ghee drops to the floor to improve his own line of sight to a different foe. He brings his blowpipe to his lips and aims a dart at the lizardfolk's unprotected left leg, but Ghee's dissatisfaction with not being able to punch the enemy prevents him from properly aiming.

(Cat Keeper and Toothless are up next.)

Cat Keeper points to the hook Toothless has sunk into Bearrik's flesh, to which the human replies: "Ready!" One thug helps the other and they jointly try to shove the bear off the stone pass.

-> Shove vs. Bearrik: 20 

-> Bearrik's contested athletics check: 18  

With little space to dig in his bear heels, and the strength of a goliath and a tavern brawler against him, Bearrik is pushed 5 feet off the overpass. Half of his body is still on solid ground, but that is not enough for the beast to keep balance, at least not on its own.

-> Bearrik's DEX saving throw {DC 14}: 19 

Bearrik manages to hang on but the lower half of his bear body is now dangling over the side of the overpass, and he is still grappled. 

DM's Screen:

(Ang is up next.)