Skye has Darkvision and happy to meet at night I think. Expecting it. She probably would feel it’s sensible to get there well before the meeting time to look at it from a few angles, in case of a trap. 

The meeting is in the Yawning portal, so darkvision is not essential. No specific time is given so you have plenty of time to scope out the tavern, inside and out. Make a stealth check and a perception check (with advantage assuming others are there helping look)

Xaul will come and provide help whenever necessary. 

Kylaski thinks this sounds interesting, so she takes over and tags alone. She isn't particularly skilled at being stealthy, but she's good at being a distraction. {especially yet distracting Sehaethas}

Damros tags along with the others. "I hear the Yawning Portal has decent food and drink."

With her cloak raised and the help of the others, Skye leads the others to the Yawning Portal. All of them are familiar with it, same as any adventurer or person who makes their livelihood in a risky way. 

She spends a while looking from the outside, for any sign of her contact. When she’s happy she makes her way quietly upstairs, to one of the shoddily railed floors that overlooks the titular well that descends from the middle of the taproom. 

The others help by taking seats at other points, higher and lower and opposite until ready to join the meeting, should it look sensible and safe to go ahead, without evidence of a trap. 

Perception: 13

Stealth: 10

Kylaski gets bored waiting, changes back to Sehaethas. Sehaethas mutters under his breath, "I really wish you wouldn't do that in public."

Skye, you quickly spot Davil at a table in the centre of the room near the well, but not too close to it. While you are observing him, you get tapped on your shoulder and turn to see Yagra there. Clearly you weren't as stealthy as you hoped. She gestures for you to follow her to Davil and he offers you (and anyone else who goes with to the table) a drink. 

Skye follows at being caught. She asks for a spirit. Strong, flammable, clear as water and hard to poison. 

After a while she gestures with one hand, as if to say ‘go on’. 

Damros will stay try to stay as 'not notice-able' as possible; listening but trying to stay alert to the surroundings.

Perception:  8

His eyes keep slipping over toward the pit in the middle of the tavern.

Sehaethas was good at not being noticeable, at least until Kylaski decided things looked interesting and took over again. For now he'll just watch from a distance.

Yagra will go to the bar and come back with a vodka for Skye while Davil starts talking. "Thank you for trusting me again Skye. I hope you realise that what happened to you was.... very unfortunate and not at all something we wanted to happen. Skeemo, our Master of Magic managed to find the traitor who betrayed you, and let me assure you, they are unable to do anything else to you or anyone else, ever again. I would be very pleased if you were to resume your services to me, and in fact have got something you could get on with right away. Additionally, I am aware you met with the Harpers earlier. I would like to make it clear to you that I have no objection to you dealing with them, as I am sure you are aware that we are trying to gain a legitimate foothold and therefore have nothing to hide from the Harpers. That being said, the Harpers don't seem to quite grasp the fact that there is two totally opposed branches of the Zhentarim here and therefore whenever anything bad happens involving the others, it reflects badly on us. It is why I like to carry out my business here in public view to show I have no ill will."

Lots of things cross through her mind. If Skeemo sorted things out then why wasn’t Skeemo here to grovel. Everything was ‘taken care of’? Legitimate business. In the open? How convenient. these thoughts and others press against her tongue as she fights an unwise decision…

But she came here for a reason, and as the moments drag on, she pushes her anger back down, and gains a deep and deadly calm. Not too keen. Not too permissive. That’ll be too suspicious. 

“I won’t be cheap anymore. I want gold, and I want it up front, if you need ‘legitimate’ porter services. And I’ve got a private crew now.” 

She leans back in her chair. 

Get money. Secure the inn. Keep hands off, and when the opportunity comes, burn down the Zhent from the inside. It’s a good plan. 

Damros sighs as he is easily distracted and gets little from the conversation going on at Skye's table.  Getting up, he moves to the bar to order a mug of cider and a meat pastie.

Xaul follows his Shadar Kai companion away from this serious business and sprawl his broad shoulders out to lean against the bar, watching the discussions from afar. 'Guess we're her private crew now then, ey?' he jests, giving Damros a nudge with his shoulder that's just a little too forceful, nearly jogging his ale. His tone then goes a little more thoughtful as he scratches his nose, muttering 'I hope she's got a plan though, since I'd hate to get roped into any messy Zhent business...can't imagine that would end well for them.'

(So annoying. I typed a response to Skye, and never sent it... time to rewrite it)

"I wouldn't have expected any different. And I have seen your crew here before when you all returned Volo's friend to him. With you willing to help a stranger find a friend, I feel like you would be happy to assist on this errand of mine. And yes, it is dangerous so I wouldn't expect for you to be cheap. But I am aware you don't trust me after what you went through. What is to say you won't take the money up front and leave? (Feel free to make a persuasion check to push for an upfront payment) That would not be good at all, for either of us. The errand in question is... simple in principle, though possibly a bit harder in practice. Someone is killing elf and half-elf sailors in the Dock Ward — three dead so far, each one decapitated by a blade in the dead of night. Look into it, will you? Methinks the City Watch could use a little help. You do not need to stop the killings. We can arrange for that, but if you can end them yourself, your reward will be greater."

Xaul follows his Shadar Kai companion away from this serious business and sprawl his broad shoulders out to lean against the bar, watching the discussions from afar. 'Guess we're her private crew now then, ey?' he jests, giving Damros a nudge with his shoulder that's just a little too forceful, nearly jogging his ale. His tone then goes a little more thoughtful as he scratches his nose, muttering 'I hope she's got a plan though, since I'd hate to get roped into any messy Zhent business...can't imagine that would end well for them.'

Damros looks at Xaul and then over his shoulder at the table where Skye was 'negotiating'.  He nodded slow before taking a large gulp of ale. 

"Crew, for certain.  Not certain how private.  I too am hoping she has some plan that will benefit us all - not just for Skye."

Taking another swig and wiping his mouth with his sleeve, Darmos looked around the room.  "Any time the Zhent are involved; it gets messy.  How deep we want to wade into that mess...  I suppose we shall find out soon enough."

Persuasion: 22

Skye shrugs. “Finders fee now. Solver’s reward later. What’s to stop me running off? Make it generous enough that I’d be foolish not to want an ongoing transactional relationship.”

"100 dragons up front now. Depending on the level of information or results you provide, your reward later will vary between another 100 dragons, up to 400 dragons. I think that should be satisfactory."

Skye sits there thinking for a moment. Not really questioning it, they need the money but she wants to give the appearance of being willing to turn it down if it is too low. She  then leans forward. "Satisfactory. Just about. I am putting my life on the line here, and my crew's life too. And a crew isn't cheap as you know." and then without another word, she holds out her hand for the up front payment, and then gets up and walks out once she receives it, waiting for the rest of you outside, filling you in on anything you might not have heard clearly over the noise in the inn.

Sehaethas well follow Skye soon afterwards. "It looks like you accepted the job. What is it?"