Majin fires at the enemy, but they manage to bob and weave out of the line of fire just in time.

Edrick is now clasping onto the rope for dear life with the crate.

Boo and Carrick are pulling Edrick up with the rope.

Eldin fires another bolt of flame out, striking the figure as they fall over again. (DCF #4: defeated, 55 damage.)

Ith has got to the crate. He can take it, but it will just be "hovering in midair" with the other two guards seeing this.

The Gun Guard steps out to shoot at Edrick.
Musket vs. Edrick: 8 vs. AC. Hit: 14 piercing damage.
(Typing)

The Dark Cloaked Figures atop the carriage quickly collect their fallen companion as their sky coach rides beside them. They quickly jump over the short gap, now out of view.

The Enforcer Guard, seeing Edrick being pulled up onto the ship, quickly attempts to grab the rope.
Athletics: 15
(typing)

At the end of the round, the lightning rail turns the next corner, as it shows that the rendezvous is in sight. It won't be long until extraction is required.

INITIATIVE TRACKER

So. Ith is going to make a run for it. He will use the surprise of the "hovering box" and dash to where he bleives are the others.

Just one more question are there guards on the way  

Eldin is near the Party skycoach. Can't Eldin use his reaction to AoO the guard that jumped on to the rope? I assume he would have to cross within striking range of Eldin to get to it.

Once we've got Eldrick up, Carrick is going to drink another healing potion.

Potion:5

Boo struggles with Carrick to pull Edrick up, hoping they are going actually get him up... so keeps checking for any surprises as best she can.

Majin will put away his spent pistol and pull out his long sword and jump across to where the DCF's are. he will take a swing at both of them 

DCF 1: Attack: 13 Damage: 5

DCF 2: Attack: 18 Damage: Unable to parse dice roll.

(Eldin's still atop carriage 4, with the enforcer on the connecting part of the carriage. There wouldn't be an AoO as he wasn't in your weapon reach as he grabbed onto the rope.)

(Majin, if you are stowing a weapon, that is your Interact with an Object for the round. You wouldn't be able to draw a new weapon unless you use your action to do so. Either drop the gun, or you don't get any weapon attacks this turn. Beyond that, there is the matter of the jump, how far can you long jump?)

In that case, can Eldin, on his turn close the distance and stab the guard hanging on to the rope with his rapier?

Ith is running. Of he becomes visible he will use the face shifting ability if he encounters a guard. 

In that case, I will use my action to reload my pistol 

Eldin, you can slip down into the connection area of the carriages (15 feet of movement overall) to get within melee reach of the guard.

Majin, IIRC you can reload the gun as one of your attacks, so can still make one shot with the pistol if you want.

In that case, Eldin will hop down to get into melee range of the guard holding on to the rope and... wait.

How much rope is between the Guard and Edrick (who has the box?)

Also follow-up question: How far away is the guard from the train?

Effectively the guard is on the rope about 10 feet below Edrick. He is off of the ground by a foot or so right now, and hanging barely away from the platform that Eldin can stand on between the carriages.

Eldin will get into melee range of the guard and strike the guard at the base of the shoulder with his rapier in an attempt to force the hanging guard to let go.

Hit: 18 Dmg: 6

I will take a shot at one of the DCF Attack: 25 Damage: 14

Majin reloads his weapon, firing a single shot out towards the DCFs. His shot strikes true, grievously wounding one. (DCF #1: 36 damage.)

Ith grabs the box and begins to hightail it out of there. The hovering crate rushes past the guard with a gun, who goes "What the!?" as it passes him. Ith sees that the sky coach is backing away with Edrick and the other crate being pulled up onto the ship with an enforcer guard just beneath him.

Eldin turns up at this point, seeing the floating crate nearby, and stabs the guard as he is holding on for dear life. (Enforcer Guard #3: 8 damage.)

Carrick & Boo pull on the rope, getting Edrick up onto deck. However, they apparently pull up the guard as well! (No, it doesn't oppose OA, it is "forced" movement. It is also why I asked for a Strength check, as it was more than just Edrick on the rope.)

Edrick, now on the sky coach, quickly moves to where Biff is and sticks the crate beside the helm, trying to keep it secure.

(Will do NPCs in a separate post)

Biff raises the sky coach lightly away to be above carriage 4 right now with a 10 foot gap between the carriage and the bottom of the sky coach.

The Gun Guard sees the crate hovering past. Unsure what is going on, he stows his musket and attempts to grab the crate.
Grapple vs. Ith: Please make a DC 20 Athletics or Acrobatics check to wrestle control of the crate away from the Gun Guard.

The DCFs appear to be retreating, their sky ship disengaging from the lightning rail. It appears that they are admitting defeat.

The Enforcer Guard upon the sky coach stands up and has his baton ready. "Y-you're all under arrest!" He calls out, seeing Carrick and attempting to knock him out with the baton. You've gotta admit, he has some gusto...
Baton vs. Carrick: 18 vs. AC. Hit: 4 bludgeoning, plus 1 lightning damage.

Despite all chances, he actually manages to hit Carrick. (Carrick: 11/54 HP)

INITIATIVE TRACKER

Eldin sees the floating crate and the guard's attempts to grab it. Eldin will rush forward and stabs the Gun Guard with his Rapier.

Can Eldin make it to him without using his bonus action?

Hit: 27 Dmg: 6

Critical Hit (Also forgot to add sneak attack damage)

Regular Sneak Attack: 2
Crit damage: 3
Crit Sneak Attack: 6

Total Damage: 17

"Don't you stupid rent-a-guards know when to call it a loss?"

Carrick is going to take two swipes at the guard.

Attack: 25 Damage: 10

Attack: 26 Damage: 11

Ith leaves the invisibility sheds off.  He tugs hard using his momentum to help, he just turns his head toward the guard. ( Acrobatics 11 )

( He will try to use  Unsettling Visage )