The darklings pause as they hear Ben and Titaani's lines, unsure of how to respond.  "O! Such brave and beautiful words!" blurts out Amidon from the wings. 
But while some remain uncertain, 11 of them continue to rush for the stairs toward Ben. 

Stagefright freezes, his eyes on Horatio with alarm. Horatio: make a DC18 Intimidation check.

Ben casts a protective ward upon himself. 

The hag takes flight upon skeletal, mechanical wings, appearing to head back to her third-story balcony (directly above Ben's shattered mirror.) "Take the princess, too," she adds.

Matilda: Where on the map are you trying to sneak to?

Everyone: Roll initiative!

Pud pops the top off of his one of his alchemical elixirs and gulps down the concoction. (OOC: +1 AC for 10 mins)

He doffs his disguise and readies his shield. The magical shield of expression frowns and sticks is tongue at the threats rushing towards them. 

He stands in front of Titaani and yells…

”Rise up you cowards! Join us! We defeated Skabatha and burnt down Loomlurch! Help us in our quest to free Prismeer!”

Persuasion: 3 (1+2)

Initiative: 8

Initiative:

Endelyn: 20
Darklings: 4
Stagefright: 10
Pud: 8
Elkhorn: 7
Gleam: 24
Glister: 14
Amidor: 11
Pollenella: 8
Titaani: 
Matilda:
Ben:
Horatio:

Ben’s Initiative:  4

Titaani's initiative: 4

Initiative (reordered):

Gleam: 24
Endelyn: 20
Titaani: 18
Glister: 14
Amidor: 11
Stagefright: 10
Pud: 8
Pollenella: 8
Elkhorn: 7
Ben: 4
Darklings: 4
Matilda: ...
Horatio: ...

Gleam suddenly becomes visible in the audience, next to her cloaked twin sister. She looks anxious, but determined, as she releases a soft bluish beam at Endelyn as the hag takes off from the stage upon her ornithopter.

Gleam: Ranged Spell Attack vs. Endelyn: 12. Hit: 9 radiant damage, and Endelyn must succeed on a Wisdom saving throw...

Matilda and Horatio should roll initiative (and act if it's 20+)
Horatio may make that advantage intimidation roll vs. Stagefright if he's enlarging.
Titaani may have an opportunity attack vs. Endelyn if she so dares.

Titaani will take that opportunity attack, using her dagger she had drawn earlier. "Didn't like our performance, huh? Well, maybe you'll like this!" 

Attack: 24 Damage: 4

Titaani sinks a blade into the hag as she lifts off on her ornithopter. "Ow!" she shrieks. "You ugly little sow!"

Initiative (reordered):
Gleam: 24
Endelyn: 20
Titaani: 18
Glister: 14
Amidor: 11
Stagefright: 10
Pud: 8
Horatio: 8
Pollenella: 8
Elkhorn: 7
Ben: 4
Darklings: 4
Matilda: 15 

Endelyn flies up to the second tier of balconies, where she lands and climbs off her ornithopter. (Dash) She scowls at Titaani. (Did that roll include crit damage, do you recall?)

Stagefright huffs, ignoring Horatio. He's had a rough day.

Titaani and Matilda may act next. (Endelyn is 50 feet away from Titaani and 60 feet from Matilda - across the amphitheater and 40 feet up.)

Matilda kept as unobtrusive as she could as she attempted to climb up to where the Hag had gone using curtains, cladding or whatever was available without being seen......

All the time thinking to herself.....this is the exact opposite of what we agreed to do, we are all going to die.....

( If Jump and Expeditious Retreat are still in effect, less than a minute I think, then she will use them to maximum effect to get up as close to Lyn as possible without being scoped ( hopefully still can use the stealth roll from earlier).

Athletics or Acrobatics if needed- 15 or 20 )

(It did not include crit damage, here is the extra roll: 6)

"What did the marionette say again...about Endelyn's weakness?" Titaani wonders out loud. "Ugh, if only I had the ability to focus and remember!" 

Frustrated, the little gnome shoots off a ball of crackling purple energy at the hag. Eldritch blast attack roll: 26 Damage: 4

Quote from queen_of_ashes19 >>

Frustrated, the little gnome shoots off a ball of crackling purple energy at the hag. Eldritch blast attack roll: 26 Damage: 4

 (I can't believe I rolled the exact same numbers twice! Here is the extra crit damage for that eldritch blast: 7)

As some of the darklings begin to race for the stairs after Ben, Matilda, blending into the crowd with her best "but I'm just a kid" guise of innocence, manages to beat them all, running with unnatural speed. She makes a single, arcanely-powered jump - straight up, nine feet into the air, and manages to catch and clamber up onto the first balcony (the one opposite Ben's.) Unfortunately, her Jump spell fades immediately afterward, and Endolyn is still one balcony up. (Expeditious Retreat remains in effect, though, provided she can maintain concentration. However, there is no stairwell up from here. Just a mirror and stairs back down.)

Titaani fires a very well-aimed missile of purple plasma at Endelyn. A perfect hit, but this hag is tough. She can take a lot more than that.

Amidor the dandelion races across the open amphitheater, jumping onto the stage in defense of Titaani, who is about to be mobbed by some of the darklings.

Glister runs out into the amphitheater, trying to get her eyes on Endolyn. She unleashes a Sun Ray:
Glister Ranged Attack vs Endolyn: 16  Hit: 12 radiant damage, and the Endelyn must succeed on a DC 13 Wisdom saving throw...

Stagefright retreats (Disengage) and races out by the wooden set cranes dangling over the precipice. 

Pud and Horatio (enlarged, right?) may act next.

(Endelyn, not shown on the map below, is one floor up from Matilda, on a similar balcony.

(Endelyn DC13 WIS Saving throw: 13)

(( Action 1 )) Horatio dashes after Stagefright.

(( Action Two )) Horatio attempts to Grapple Stagefright ( Athletics = modified 20 )

(( Bonus Attack from Unarmed Offhand )) 19 to hit, 6 damage

Horatio runs after Stagefright, attempting to grab one arm while simultaneously punching him in the face.

Horatio chides, "Are those hags worth dying over, because I will kill you if I must." There is no anger or volume to his words, only determination. 

"Rizzo, It's go time!"

The tiny clockwork humming bird buzzes and takes flight from its hiding spot in Pud's smock. It flutters in figure eights around Pud, Amidor and Titaani. Pud moves to interpose himself between Titaani and Darklings. He attempts to conjure a mote of fire with a new spell he's been practicing, but messes up the incantation and something goes awry.

Action: ranged spell attack Fire Bolt. To hit: 8 (1+7) for 11 damage.

Frustrated at his mishap, Pud orders Rizzo to attack. "Get 'em, Rizzo!" The tiny mechanical contraption halts its flight, hovers for a brief moment before  darting at the closet darkling, delivering a concussive blast of energy upon impact.

Bonus Action: Ranged spell attack. To hit: 23(19+4) for 6 force damage.

Matilda looked at the mirror frames and her daggers and figured it was worth a shot to see if she could climb them by stabbing into the wood and hauling herself up.....

( Athletics?)

Horatio chases Stagefright out onto the loading dock before trying to grapple him and punch him. Stagefright: Contested Strength check: 16  
Horatio's punch lands, bloodying his face. "Ow!"

Rizzo blasts one of the darlings rushing the stage. It seriously injures the strange little dagger-wielding fey.

Pollenella buzzes across the amphitheater to protect Amidon on the stage. Squirt just flies in anxious circles in the air, squealing "Oh! Oh! Oh!"

Ben is up next! He can't see Endelyn from where he stands on the balcony, but he can see at least a half dozen darklings running for the stairs to assault him/

Ben:

”Yes!  Let us assault the dreary hag! She flees upstairs!” says Ben encouragingly to the approaching darklings.

Ben grabs the sturdy bench and runs back into the orrery room towards the lightning rod at its center, hurling the sturdy bench at its most vulnerable spot.

Athletics:  9

Ben shoves the bench through the gaping hole in the broken mirror, and then tries to hurl it at the lightning rod at the center of the Orrery. Alas, his throw is short, for it's a heavy piece of furniture, and the electrified machine is some 30 feet in radius.

Some of the little darklings begin to swarm the stage, others swarm up the stairs toward Ben (but can't quite reach him yet.) Still others stay where they are in the audience, seemingly unsure of what to do.

One of them (the wounded one), circling behind Pud, tries to Grapple Titaani:
Darkling Grapple Attack: 16
(Titaani: make a contesting Strength (Athletics) or Dexterity (Acrobatics) check)

Gleam races out into the middle of the amphitheater next to her sister, and fires a blue ray at Endelyn:
Gleam: Moon Ray Attack: 15. Hit: 18 radiant damage, and Endelyn must succeed on a DC 13 Wisdom saving throw...