(I think that's everyone but Cordelia, whose signature indicates she's out tonight. We'll pair her with Gordra in the barrel until she has a chance to log in.)

Turn order:
Amaruve 21
Jean 19
Hobgoblin 9
Perspicacious 5
Bandits 4
Gordra and Cordelia 2

There's one mean hobgoblin to the left (West) and three ridiculous bandits to the right (east). Might be a couple more bandits in the barrel

(How far to the nearest bandit?)

(Edit: the triangle is 50 feet, but I'm wondering if bandits having exited the barrel are closer, and if we may be closer having done the same.)

(I can move 40 feet and reach 5.)

Sure, let's say you've closed 15 feet toward the center. Two bandits and the hobgoblin are next to their respective barrels. One bandit has started charging you and has covered 10ft. He's now 25ft away

(before we start mauling, just remember you're the good guys in this story and those are sentient creatures of unknown agency)

(If you're avoiding inflicting fatal wounds, specify how you plan to attack them)

Amaruve sees Jean is ready. The big guy seems to be her target. He wants to wait a beat, but he won't squander his opportunity. If they wait they'll lose control of the situation. He trusts his instinct, and moves for the charging fool... He should have kept with his pack for defense. Should Amaruve have done the same? As soon as the thought enters his mind he's already upon the enemy.

The terrible, reptilian, bird, bear, monster that is Amaruve screaches a high, hissing cry that ends in the rumbling note of a bear's roar.

He Pounces and strikes with his claws. His instinct is to take the neck, a quick kill, to bring home dinner... But this isn't the jungle. He isn't hunting. These are men. He keeps his senses. He is not a bear. He is not a beast. He tries to put his weight and momentum into the mans center of mass and end his willingness to continue. The speed of this body is incredible. He strikes again and again, Multiple Attacks with tooth and claw, grabbing the enemy's leg and shaking it like a chew toy. If the enemy gives in, he'll continue onto the next.

He makes three attacks, hitting
21 for 6, and
16(adv. If prone 12) for 8 slashing with his Claws (Str save DC 12 or fall prone on first claw hit), and
21(adv. If prone 17) for 9 piercing with his Bite

If or when the first enemy falls prone (if not unconscious) Amaruve makes an additional non-lethal Bite, hitting 19(w/ adv.) for 6 piercing.

 Pounce:

 Multiattack:

Amaruve charges the sprinting pirate. One second before their collision, the pirate's eyes widen in sudden realization that this monster isn't just someone in a costume. 

Amaruve sails through the air in a mighty leap, four sets of claws oustretched and maw wide open. He comes upon the pirate...

...And passes straight through it. Amaruve lands on the ground in a slide, 10 ft from the Bandit barrel.Looking up at his foe, Amaruve sees a faint haze in the general outline of a pirate. The illusion no longer effective against him, the druid now sees a 3ft high octopus-like creature moving with incredible speed for something so small and gelatinous. Round, black eyes surround its fleshy surface, and it wobbles back and forth as it continues its path toward the rest of the party. It sports a pirate hat like the one worn by the rest of the "pirates".

Amaruve, the creature is 20ft from your barrel and 20ft from you. You are out of motion, but you have a chance for a final action

(Sorry that you went to all that trouble on your rolls, BDaddLy- I tried to think of a way to incorporate them, but couldn't make it work with the fiction. Feel free to copy/paste that block of moves for future use)

(No trouble rolling. You got me good. I was just about to comment that with all those dice at level-2 you can tell, I just like the sound of the dice on the table.)

Amaruve skids through the pirate illusion and hops to his feet turning left and right in confusion like a dog chasing an unthrown tennis ball.

He makes a dash to return to his allies.

(Awesome. I'm assuming Amaruve skirts the homunculus (yes, it's a homunculus) to avoid provoking an opportunity attack?)

The crowd erupts in laughter and jeers in sections. Other areas of the arena are curiously quiet- they too are beginning to realize this is not a costume.

Jean, the creature is upon you and decreasing in speed. You still see a pirate, but given what you just witnessed I'll give everyone (yourself included) a bonus investigation or insight roll here to pierce the illusion before you move. 

Perspicacious watches as the bear passes right through the pirate. "Mammon's gold," she curses. "I need a drink." Sans beverage, she takes a moment to look more closely at their opponents.

Insight: 19

(OOC Pretty sure I can't roll above a 5 to save my life...)

(Nah, Amaruve will risk the opportunity. Opportunity for Intel.)

Amaruve tries to sniff out the details of this ruse. (Insight: 6)... But he knows an honest to goodness gladiator arena when he sees one (as the authority on 5e arena combat, I know this is the real deal.)

Investigation: 7

(Oof, sorry, AP. A crit miss. You are distracted by the warmth coming from your coin and you see nothing to explain Amaruve's passage through the advancing pirate. 

(No kidding, BDaddLy. I didn't even think about that! At the risk of making a fool of myself in front of the master...)

The creature continues its speedy progress toward the party even as you pass it by, Amaruve. However, you notice that its tentacles are starting to blacken and a haze of smoke has begun to pour from its eyes...

Amaruve feels inspired. He sniffs again. (Insight: 25)

With a 10 and the underlying knowledge that he's dealing with illusions, Amaruve sees through the glamour of the pirates to observe his enemy's true face...

Which he can act upon in his next turn!

(I think the rules state that knowledge of the illusion grants advantage to insight/investigation of it, so you still have inspiration)

Jean! It's your turn!

Extra planar weirdness might not have been Jean's forte, but she had dealt with the occasional Illusionist on the streets of Waterdeep. She wasn't quite sure what manner of beast lay behind the illusion of the pirate so she planned to take long wide swings through the entire space, just to be sure. She wasn't quite sure of the rules of this particular contest, so she decided she'd stop attacking opponents once they were unconscious.

Jean put on a burst of speed and charged into the 'pirate' with her longsword chopping downwards at her opponent's center-line.

Attack: 18 Damage: 5

Jean's sword (which, luckily, remained at her side through to this leap) cuts cleanly through the air and into the pirate. Where normally she would expect resistance the sword instead carries downward to the bandit's navel before sinking deeply into something as soft and squelchy as a trashbag full of pudding. Immediately, the illusion of that pirate fades from everyone's vision, and the many-eyed construct, cut nearly in half, melts into a puddle of smoking beige goop.

The hobgoblin smirks and takes a rather large longbow from its back. It drops (surprisingly gracefully) to one knee and looses an arrow at Perspicacious.

Attack: 18 Damage: 10

Perspicacious is struck heavily by a large arrow, the shaft of which is now protruding from her right shoulder. The coin in her hand tumbles to the ground from her numbed fingers. Through the pain, Perspicacious notices that a golden glow seems to be surrounding the coin. Thin spider-silk strands of light seem to extend from it to each of the people standing in the arena. The threads reaching her party members are faint, muted. The strand extending to the hobgoblin is bright and thick, however. To her eye, it almost looks as though something could be pushed along that track and directly into the hobgoblin's heart...