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Ok, if the party is going to split, I'm sure you would have considered the pros and cons. I would need to know (1) who is going with who (2) which master each subteam is going to visit, or alternatively to ask around the streets for information, and (3) which subteam is taking the mayor's letter. It would provide bonuses for some encounters but if you're splitting, then only one subteam will benefit from it. When we roleplay the respective sections though, I may take one subteam at at time to preserve my sanity. :) And also I think it would help you to keep the stories straight without interweaving accounts.

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So far it looks like...
GAB!: Dependable Drummady
Kebro: Haberdasher Petrellano Pindlion
Rithon: Willing to go with someone.
Krennel Halfstool: Pricknettle's Potions and Poultices
Yen Wu: Haberdasher Petrellano Pindlion
Rel Kalorsk: Undecided.
The letter: currently unassigned.
Since a few of us are heading the same direction, being the Drummady/Haberdashery/Witch's End tavern, we could work together on those 3 and just take them down one at a time.
If Krennel wants to head for Gunty's Hearty Breads after Pricknettle's Potions, we could let him have the letter and try to get those two areas. That is, ofcourse, if Rithon and Rel do not go with him.

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I would personally vote against splitting the party - last time that happened in a game, we ended up losing two PCs. but if everyone insists, Rel will just gather info around town on the apprentices.
Diplomacy: 1d20 + 6 ⇒ (16) + 6 = 22

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I'm good staying together. It just looked like we were splitting up, and it is totally a first level thing to do. We can all go shop for hats.

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that makes sense, I'm down with sticking together. Might make it easier story wise. That way we can all use the letter benefits.

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In that case, I think GAB! should pick the first location... since it only has a finite time in this form.

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In that case, Drummady then Haberdashery then Witch's End Tavern then GAB! can park and wait at the tavern?

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sounds good!

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Getting to the Dependable Drummady’s takes you almost halfway across the town. Although cobblers, especially in a small town like this, would not be expecting rousing business, but it appear good, with a few customers coming in and out. Heeding the mayor's advice, you wait briefly until you are sure there's no other customer present before entering.
Behind the counter was a relatively short human female with dark auburn hair. In one hand is an awl which she is using to thread thick thread through the leather of an unfinished shoe. She looks up, frowns briefly at the unfamiliar faces, before returning to her prior look that is best described as grim resolve.
She speaks in a soft but firm voice. "Welcome to Dependable Drummady's. Do you need new shoes? Or an old pair fixed?" Although not rude, she is direct and to the point.
(Please include the relevant social skill rolls.)

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"Greetings, ma'am. We were actually looking into possible information about the disappearing apprentices of Saringallow, on behalf of the mayor. Might we have a word?"
GAB! also shows the note from the mayor.
Diplomacy: 1d20 + 1 ⇒ (6) + 1 = 7

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Drummady frowns briefly, before replying suspiciously. "Yes, Pavolus has been absent for a few days now. That is my family business, however, and we will deal with it. If you are not here for shoes, then I am not sure how much more I can help you." Almost immediately, you see her muttering under her breath.
The diplomacy check is obviously not good enough. :)

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Perception DC18: 1d20 + 7 ⇒ (14) + 7 = 21
"Why did your husband chase them away?"

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perception: 1d20 + 11 ⇒ (13) + 11 = 24
Kebro pulls down the bandanna and smiles.
"We are just looking to help, miss. We mean nothing but the utmost respect. When was the last time you saw your apprentice?"
diplomacy: 1d20 - 1 ⇒ (10) - 1 = 9

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As the pathfinders enter the shoe shop, Rithon begins to poke around and look at the wares as the other pathfinders talk. Appraise: 1d20 + 5 ⇒ (5) + 5 = 10 I took a rank in appraise, and gosh darn it- I am going to use it!
Poff. Average at best. This apprentice has much to learn...
He approaches the counter with the others.
"Yes yes. We came all the way from Absalom to help. Yes it is far. No, it wasn't comfortable"
Diplomacy to Aid: 1d20 - 1 ⇒ (8) - 1 = 7

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Think we should level up our Diplomacy when we advance to the next one?

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Sense Motive : 1d20 + 8 ⇒ (10) + 8 = 18
Diplomacy : 1d20 + 6 ⇒ (3) + 6 = 9
We're just interested in helping - puzzles like this can be like a tapestry - find the right string to pull on and the whole thing unravels. And you never know what that string will be, so any information you can offer would be most appreciated.

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Looks like diplomacy isn't this party's strong suit...
"Why did your husband chase them away?"
"What? Oh." Drumaddy's face flushes briefly when she realises that you have overheard her, then she straightens herself and stiffens her back. "That Petrello! If Pavolus and Betrona have run away, it would all be his fault! Always so harsh. So severe! He faults their work, but is blind to his own incompetence! Even tries to control their friends! At their age! Always forbidding them from meeting Gellion. Thinks he's not good enough for them. Has he looked at himself!" She fumes as she unloads onto you. Clearly she has bottled this up for some time.
However, she quickly collects herself, and stiffens as the Pathfinders pushes further. "But I over-react. I'm sure my two children will return soon. There is no mystery here."
Krennel starts to look at the wares on display. "Got anything in a 10?"
Seeing someone who is actually interested in her wares, she turns to serve the half-orc. "Of course. What kind of cobbler would I be otherwise."
She brings Krennel over to the shelves. "Now you could simply get one of these off the shelves. They might not fit well, but if you need something urgently, or looking for something economical, I am sure I could help you find a matching pair. But if you have the time, and the funds, I could take your measurements and..."
She stops here as she comes across a pair of bright yellow boots, and sighs. "Petrello knows nothing about his son. Or his friends. Pavolus made this pair, as a trial before making another for Gellion as a gift. Gellion is smart and charismatic. Always taking care of the whole group, Pavolus just wanted to do something to thank him in return. How kind-hearted is my son!"
She quickly shakes herself out of the reverie. "So what would it be? One of these for 5 silver pieces. If you want a custom-made one, it would be 2 gold pieces, and a week."

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Looks like diplomacy isn't this party's strong suit...
Or dice, for that matter.
GAB! begins writing down notes in her its notebook.

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Krennel muses over the offer. Her work is nothing close to what I would find at home. Still, the work-a-day style could be something a conversation starter. "Well, I think a week is decent amount of time to wait for a custom pair."

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"Oh. Yes. Shoes. I had lost... I had lost track of things again. It is quite possible that the children are just being children- yes. Petrello though, is he the cobbler in charge, as it were? You mentioned something about his own incompetence- what, exactly, is he incompetent with?"

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While I have no need of new shoes currently, your craftsmanship is superb. Should I ever be traveling this way and in need, I'll certainly stop in.
After concluding their talk, Rel will ask outside,
Where to next? I vote we head to Haberdasher Petrellano Pindlion

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"That sounds good to me friends."

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"Elytra agrees. I think she likes you."

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"Blorp- I mean, thank you." GAB! says the first in joy, then stammers and changes tone to match what would be expected.

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Alright, I'm back in action! Thanks for your patience.
"Oh. Yes. Shoes. I had lost... I had lost track of things again. It is quite possible that the children are just being children- yes. Petrello though, is he the cobbler in charge, as it were? You mentioned something about his own incompetence- what, exactly, is he incompetent with?"
Drumaddy sniffs loudly at this. "A cobbler? In his wildest dreams! It was my craftmanship that brought in the business. After we split, he set up his haberdashery. His hats look more like shoes than his shoes ever did," she comments acidly.
She then seems to realise that she is unloading on complete strangers and straightens up, remaining professional for the rest of the interaction. She takes over the coins and set an appointment with Krennel and Yen.
---
Petrello’s Haberdashery is just across the street, but what a difference. The shopfront is run down and when you enter, you find the mess inside even worse. Dusty fabric lie on random corners about the floor, and tangles ribbons are stuffed haphazardly on the shelves.
A unkempt sour-looking portly middle-aged man sits restlessly behind the counter. He visibly perks up when the doors open, but he immediately scowls when he sees strangers enter his shop.
"Yes? What do you want?" is the rude greeting he offers. A salesperson he clearly is not.
Since diplomacy isn't the strong suit in this party, I'll cut you guys a bit of slack. I'll take the highest roll as the lead, and the rest as aid attempts.

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"Information about your son would be nice. I can help clean up around here a bit in exchange." GAB! offers, flexing.
Diplomacy: 1d20 + 1 ⇒ (17) + 1 = 18

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Kebro walks into the shop and gracefully sidesteps the piles of stuff.
"We are charged by the mayor and the Pathfinder Society to get to the bottom of the missing children. Any kind of information you can think of will be of great help sir. "

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The half orc walks into the shop and looks around. He puts his hands on his hips. "Well I'll be damned! They DO look like shoes. Laughably atrocious."
Diplomacy (aid): 1d20 - 2 ⇒ (11) - 2 = 9

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Kebro walks into the shop and gracefully sidesteps the piles of stuff.
"We are charged by the mayor and the Pathfinder Society to get to the bottom of the missing children. Any kind of information you can think of will be of great help sir. "
"Bah! If you are looking for Pavolus, you have to ask his oh so smart and successful mother, since the Council said that I am to stop bothering them!" he replies with venom dripping in his voice. "And he's probably dragged Betrona into whatever nonsense they've gotten themselves into. It’s that apothecary boy’s fault. He’s a bad influence, that one!"
Keep the diplomacy aids coming though. I'm just responding for now, but the aids could tip it over.

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Diplomacy: 1d20 + 6 ⇒ (4) + 6 = 10
Sense Motive: 1d20 + 8 ⇒ (4) + 8 = 12
It sounds like the council hasn't been treating you well - but that is no reason to refuse us. We are here to help and need all the information we can get to do so.

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Sense Motive: 1d20 + 1 ⇒ (20) + 1 = 21
"Forget your pride, Mr. Petrello. Your son could very well be in danger, and anything you can tell us may help us make certain he is returned safely. Is the life of your cherished boy not enough to turn away the bitter resentment?" GAB! tries to plea to the concerned father in Petrello.
Can I keep my diplomacy from earlier?

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Oh yes. Just that not everyone else has rolled yet. Waiting for all the diplo rolls to come in before resolving.

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Sense motive: 1d20 + 2 ⇒ (2) + 2 = 4
"We are only looking to help in any way we can sir. Are the apprentices a close-nit group?"
Diplomacy aid: 1d20 - 1 ⇒ (4) - 1 = 3

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Sorry guys, that's not going cut it.
Petrello's face starts flushing and you can feel his hackles rising. "Git! Git out! What is between me and my children is my business. We don't need pity from you out-of-towners! Out!" He comes round the counter and practically pushes you out of the shop.
To clarify, Drumaddy and Petrello have two children: Pavolus (male) who lives with Drummaddy (mother), and Betrona (female) who lives with Petrello (father). When I was playing this, I got quite confused especially in PBP, so hope this helps.
Seeing how short this encounter is, I estimate you can visit 1-2 more masters before Gab! reverts. So where to next?

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Our dice suck! TT_TT
"To the tavern, everyone?" GAB! says while outside the store.

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Sense Motive: 1d20 + 0 ⇒ (19) + 0 = 19
Diplomacy: 1d20 - 1 ⇒ (15) - 1 = 14
"Oh, right! There was something I was going to ask but..." and the sentence trails off as Rithon begins to try and find some unidentified object in his belt pocket.

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Ah, going to retcon a bit since I missed that Rithon hadn't gone yet. You literally needed that one more aid to get through.
Just as the Pathfinders set off, suddenly the door opens up behind you. Petrello steps out, his demeanour considerably deflated from earlier. He looks at you uneasily, then stutters, "It... it must be Gellion and Nolaria, getting the other apprentices into some sort of trouble. I forbade her, but at this age, they just don't listen. I am sure Betrona went and met with her friends anyway. Maybe in the orchard. Or the graveyard. These kids think it's cool to hang out there. If she had only listened to me... if both of them had just listened, none of this would have happened. Please find them." As if ashamed of what he had just shared, he quickly returns back to the shop and shuts the door. You hear the turning the locks behind him.
(Still going to the tavern.)

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I meant to ask if you are still planning to go to the tavern with this new information. Question mark instead of a full stop. :P

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if we can make it to another shop with GAB! in this form we should get some more info. If not we can still go to the cemetery or orchard with GAB! in ooze form.
Kebro turns and thanks the shopkeeper with a tip of the hat.