Titaani falls ungracefully into Ben's sheet, and rolls out. "Whew! Thanks Ben!"

She looks back up and gives the kids a wry smile. "See? It's perfectly safe!"

Ben:

”Nice save,” says Ben.  “Here, help me hold this sheet out wider so we can catch them more easily if they fall,” he adds.

Pud looks down at Titaani's flailing spectacle, and of Ben's mildly bleeding wound from his fall. "Uh, uh." He shakes his head. "Nope."

Horatio waits until the sheet is better secured before leaning in to Pud. "Look, I get it. But how far would you go to get free of this place? Cuts and bruises aren't nearly as bad as being someone's slave. You can do this."

(( Persuasion attempt = Nat 20! -1 = 19 ))

Laughing a little, Titaani moves to help Ben with the sheet. 

Matilda grins, " Just like falling off a log."

"Fine," sighs Pud. He climbs out the window and gingerly tests a branch. (DC8 Dex check to climb down: 14). 

Brottor nervously follows. (DC8 Dex check to climb down: [roll]1d20[/roll]).

Pud successfully reaches the bottom without another disaster. "Yes!" He shouts in victory. 

Brottor attempts to follow. (Brottor reroll:  DC8 Dex check to climb down: 13).

Brottor successfully joins him. They look back up. Who's next?

Horatio climbs down last.

(I think that's everyone else first, if not he'll have gone last)

(( Dex Check = 13, in log ))

Matilda Dex Check- 22

Horatio and Matilda join Ben, Titaani, and the two boys on the top of the log. From here, it's easy enough to clamber down onto the ground. Except...

"Hello, children!" calls Granny from below, looking up through the tangle of branches. "Why are you on my roof? And why are you abducting my workers?"

She appears as you remember her from earlier – a short, thin, gnarled woman swathed in a tattered dress with petticoats. Cracked white face paint plasters her features, with crimson splotches on her cheeks and thick mascara coating her sparse eyelashes. Underneath her makeup, her flesh is textured like rotten bark and infested with wood lice and fungus. The windup key sticks out of her back; it turns slowly.

Beside her stands Chucklehead, his arms crossed, looking irritated.

Ben:

Whispering to Matilda and Titaani, Ben urges, "Take the children and go down the other side of the tree to the pumpkin patch.  Meet up with the others and get to safety if you can.  I'll try and stall here."

Moving over to the side of the top of the tree where Granny waits below, Ben does his best to block her sightline to the smaller ones behind him.  He says, confidently, "Hello Granny Nightshade.  You can imagine my surprise when I found out your workers are actually involuntary child laborers who were stolen from their families!  By the rule of Ownership, I was duty-bound to restore the children to their proper owners--themselves and their families!  Of course, you are free to attempt to negotiate terms of service for proper recompense with their parents once they are reunited, but I doubt given your behavior to this point they would be amenable to such an arrangement."

As he speaks, Ben moves and shifts in place, gesturing and speaking dramatically, trying to keep their attention on him and provide cover for the children to escape.

Performance if applicable:  12

Titaani gives Ben an angry glare. "Oh no, you must be crazy if you think I'll ever leave you here to die." 

(question for the dm - can I dismiss Tiny from this distance and make him reappear within 30 ft of me?)

Matilda nodded slightly to Ben and began leading the children the way indicated while Ben and Titaaani distracted her.

Stealth- 10

(can I dismiss Tiny from this distance and make him reappear within 30 ft of me?)

(I don't see a range to this dismissal, so I'll allow it!)

Matilda gathers the boys and leads them toward the staircase, but not without Granny noticing. 

Granny pulls out a small, silver whistle and blows it. It's extremely high-pitched. Chucklehead winces and begins to climb the side of the massive log.

"I love to negotiate, but not for my own property. I do not tolerate thieves," she replies.

(Combat or no, timing is key here, so it's time to roll initiative!)
Granny: 1
Chucklehead: 9
Boys: 11

Ben:

Initiative:  11

Still trying to keep her attention on him and not the kids behind, Ben replies, “Then I suggest you avoid mirrors.  We have a word for those who regard other people as their property—slavers.  Stealing children from their homes and enslaving them is about as bad as thievery gets.”

Initiative:
Chucklehead: 17  (trying to climb up the log)
Ben: 11    (grandstanding and distracting)
Granny: 8  (blowing a whistle)
Horatio: 6. (just finished climbing down)
Boys: 5   (pleased with themselves over their climbing prowess)
Matilda: ?  (leading the boys away)
Titaani: ?  (summoning Tiny, perhaps)

Matilda Initiative: 10

It Titaani can, she will summon Tiny before initiative starts. 

Initiative: 4