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If Jenya's delaying until later in the surprise round, Oster would charge the shaven-headed woman rather than just approaching her. In which case he'd have to wind up one square south of where I put him.
If that's the case:
longsword, charge, PA: 1d20 + 5 + 2 - 1 ⇒ (3) + 5 + 2 - 1 = 9
slashing, PA: 1d8 + 4 + 2 ⇒ (8) + 4 + 2 = 14

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Garret moves up behind Jenya, shortbow in hand. Noticing the unengaged black haired woman at the back of the rival group, the halfling makes her his full focus and looses a shot at her.
Shortbow: 1d20 + 6 + 2 + 1 ⇒ (6) + 6 + 2 + 1 = 151d4 + 2 + 1 ⇒ (1) + 2 + 1 = 4
Move action to move, swift action to make black haired woman his rangers focus and standard to shoot same woman with rangers focus and point blank shot.

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Garret moves up behind Jenya, shortbow in hand. Noticing the unengaged black haired woman at the back of the rival group, the halfling makes her his full focus and looses a shot at her.
[dice=Shortbow]1d20 + 6 + 2 + 1; 1d4 + 2 + 1
Move action to move, swift action to make black haired woman his rangers focus and standard to shoot same woman with rangers focus and point blank shot.
It's suprise round, only a single action allowed.

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Fine :)
Before the gang members knew what's going on most of you already took action to protect your important freight. Reginald and Tabitha strengthen the group with their magic and songs. Oster charges Dulay (the bold lady) but is not able to connect to her. Jenya moves closer to the gang and points at them with her pistol. Garret also comes closer, dancing on his toetips, ready for the next action.
Init. Dulay (bold woman): 1d20 + 1 ⇒ (4) + 1 = 5
Init. Weaver (pirate): 1d20 + 3 ⇒ (7) + 3 = 10
Init. Ledford (blonde halfling): 1d20 + 2 ⇒ (18) + 2 = 20
Init. Fosta (black-haired woman): 1d20 + 2 ⇒ (18) + 2 = 20
Init. Jenya: 1d20 + 6 ⇒ (13) + 6 = 19
Init. Hans: 1d20 + 4 ⇒ (3) + 4 = 7
Init. Reginald: 1d20 + 2 ⇒ (11) + 2 = 13
Init. Oster: 1d20 + 2 ⇒ (20) + 2 = 22
Init. Garret: 1d20 + 4 ⇒ (15) + 4 = 19
Init. Tabitha: 1d20 + 2 ⇒ (8) + 2 = 10
Round 1
Oster
Ledford
Fosta
Jenya
Garret
Reginald
Weaver
Tabitha
Hans
Dulay
Deandre Dulay (bold woman) - Cleric of Norgorber 1
Halli Fosta (black-haired woman) - Sorcerer 1
Larkin Weaver (pirate) - Rogue 1
Ledford (halfling) - Barbarian 1

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Oster, upset with himself over his poor showing, brings his sword around for another swing,
longsword, TWF, PA: 1d20 + 5 - 2 - 1 ⇒ (12) + 5 - 2 - 1 = 14
slashing, PA: 1d8 + 4 + 2 ⇒ (5) + 4 + 2 = 11
and follows it up with a bash of his shield.
shield bash, TWF, PA: 1d20 + 5 - 2 - 1 ⇒ (17) + 5 - 2 - 1 = 19
bashing, shield bearer, PA: 1d6 + 2 + 1 + 1 ⇒ (2) + 2 + 1 + 1 = 6
And then 5' steps out of his allies' line of fire. If Dulay is down, Oster will instead step into her space. If she goes down from just the sword, Oster will step into her space between attacks and bash Larkin.

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Oster swings his longsword and bashes his shield, but only the shield hits it's target. Dulay has now a big laceration on her head. I hope I put Oster in the right field.
Ledford and Fosta act. Fosta draws her crossbow and loads it with a bolt. Ledford starts raging and attacks Oster.
Greataxe, PA: 1d20 + 5 - 1 ⇒ (15) + 5 - 1 = 19
Damage, PA: 1d10 + 4 + 2 ⇒ (4) + 4 + 2 = 10
Round 1
Oster
Ledford
Fosta
Jenya
Garret
Reginald
Weaver
Tabitha
Hans
Dulay

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Jenya focuses her shot on the bald woman Oster just bashed.
Point blank shot on touch with up close and deadly (inspired): 1d20 + 7 + 1 ⇒ (15) + 7 + 1 = 231d8 + 2 + 1d6 ⇒ (1) + 2 + (2) = 5
Edit: And with her move action she reloads with a paper cartridge.

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In the interest of playing it fair, I'm happy to keep the attack and focus I've already rolled on the black haired woman for my attack. If that's okay that's a 15 to hit and 4 damage if that hits?

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Round 1
Reginald pushes past both friend and foe, heading straight for the one-eyed fellow in the back before he can act. Drawing an AOO from Ledford, if I understand correctly.
"Yield and your lives will be spared." He attempts to trip the man. Trip vs. flat-footed: 1d20 + 4 + 2 + 1 ⇒ (2) + 4 + 2 + 1 = 9. But fails quite miserably.

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It did. But I had the wrong AC listed in my statblock, so initially it looked like it hit me. And given how much damage that guy swings for, I'm really glad I revised Oster to use a heavy shield instead of a light one.

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If Oster's AC is 20, then it was a miss.
Garret shoots his arrow at Fasta and hits her hin her shoulder. Reginald moves past Oster and tries to trip Weaver, but Weaver knew what's coming.
AoO Ledford
Attack Greataxe: 1d20 + 3 ⇒ (6) + 3 = 9
Damage: 1d10 + 1 ⇒ (9) + 1 = 10
Ledford tries to block Reginald with his Greataxe, but is not successfull.
Weaver steps forward and tries to ram his rapier into Reginald.
Attack Rapier: 1d20 + 2 ⇒ (3) + 2 = 5
Damage: 1d6 + 2 ⇒ (3) + 2 = 5
But the rapier goes into the space between Reginald's arm and chest.
Round 1
Oster
Ledford
Fosta
Jenya
Garret
Reginald
Weaver
Tabitha
Hans

Standard Pregen |

Hans moves forward, rages, and attempts to hit Mr Moustache!
Greatsword, Rage, Inspire: 1d20 + 5 + 2 + 1 ⇒ (10) + 5 + 2 + 1 = 18, for 2d6 + 10 + 3 + 1 ⇒ (2, 1) + 10 + 3 + 1 = 17 Slashing damage.

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Tabitha runs ahead, getting to the right of Jenya and throwing her hand out, muttering an incantation as she focuses on a stick of butter from her components pouch. A flash of magic later, and the space beneath the pirate-looking man is covered in a slippery magic substance.
Grease covers a ten-foot square, so the space Weaver occupies will be the top left corner. This unfortunately keeps us from engaging Fosta in melee without moving at half speed through those tiles with a DC 10 Acrobatics. Weaver also has to make a DC 15 Reflex save or fall, which I'm not sure because it's 7 AM, but I think that means he provokes an AOO if he does.

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I was not able to find something about an AOO for falling, only for standing up which is a move Action and provokes an AOO.
Tabitha steps next to Jenya and mutters a few words. A short moment later the floor beneath Weaver becomes slippery.
DC15 Reflex Weaver: 1d20 + 5 ⇒ (19) + 5 = 24
Weaver does not have any problems balancing the slippery ground.
Round 2
Oster
Fosta
Jenya
Garret
Reginald
Weaver
Tabitha
Hans

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Oster will drop his sword and pull out an alchemist's fire. If Fosta starts casting anything, he'll throw it at her.
readied touch attack, 20' range: 1d20 + 3 - 2 ⇒ (14) + 3 - 2 = 15
fire damage: 1d6 ⇒ 6
more fire damage next round: 1d6 ⇒ 6 Extra damage avoided by taking a full-round to roll a DC 15 reflex to put the fire out.

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Oster grabs an alchemist's fire from his pocket and prepares to throw it at Fosta.
Fosta shoots a crossbow bolt at Reginald.
Crossbow Attack: 1d20 + 2 ⇒ (16) + 2 = 18
Damage: 1d8 ⇒ 3
She then puts the crossbow aside.
Round 2
Oster
Fosta
Jenya
Garret
Reginald
Weaver
Tabitha
Hans

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Garret maintains his focus on the black haired woman, loosing another arrow from his shortbow.
Shortbow: 1d20 + 1 + 2 + 1 ⇒ (13) + 1 + 2 + 1 = 171d4 + 1 + 2 + 1 ⇒ (2) + 1 + 2 + 1 = 6

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Nice shot Jenya says in appreciation as she turns her attention to the last foe standing.
Point blank shot on touch with up close and deadly (inspired): 1d20 + 7 + 1 ⇒ (7) + 7 + 1 = 151d8 + 2 + 1d6 ⇒ (5) + 2 + (6) = 13

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Garret moves over to the body of the black haired woman, attempting to stabilize her.
Heal check: 1d20 + 2 ⇒ (6) + 2 = 8
Heal check: 1d20 + 2 ⇒ (20) + 2 = 22
Gets it on the second attempt if that's fast enough.
"I don't really fancy her life on my hands, despite her transgressions. I'll go get the watch, you'll have plenty of time to get anything of value."
Garret wipes his hands clean, before heading out to get the watch to detain their surviving attackers.

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Well, let's see what they have in their pockets
Dulay carries two potions, a masterwork chain Shirt, a short sword, a dagger, a gray mask and an unholy symbol.
At Fosta's body you find two potions, five scrolls, a wand of disguise self (5 charges), a dagger, a light crossbow (+18 bolts), fan of pigeon feathers and a small pouch of trimmed fingernails.
Weaver has an elixir of hiding, a chain Shirt, a rapier, a dagger, a Notebook of jokes, ink, quill and his and puppet.
Ledford's body has a masterwork chainshirt, a greataxe, a blox of wax, a comb and a bottle of Whiskey and four silver cups.

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Tabitha finishes singing
"If we let any of them live, we should at least do the right thing and strip them of anything they have. That'll keep her from menacing anybody for a while." She joins in the searching of their bodies, intent on leaving the survivor with nothing to do any damage with.

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Jenya sighs Considerin' what the bald lady has on her I don't think these guys were planning on taking our stuff and donating it to the needy. Let's go with Garret and then head straight to the venture-captain. Don't feel like hanging around dead bodies.

Standard Pregen |

Hans pulls himself to attention, and salutes, before breaking out into a broad grin.
"Indeed we did, sir! Encountered some trouble along the way, but nothing we could not handle; right, guys?"