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As if on cue the city bells sound three times.

Evenwood turns to the group and says it's time to take the plunge and starts moving towards the well.

"If we must." Alecia agrees, moving to the bucket while checking her weapons.

"You will pay for our descent now?" Jim questions Sue as he turns to follow Evenwood and Alecia to the bucket-like apparatus.

"Yes I have that covered." Sue heads to the bar.

Does the wizard have a cantrip to keep time with?

"No I do not have a cantrip that tells the time and I`m wondering how we will keep time", replies Evenwood to Sue as he looks down at the well trying to see if the whole party will be able to fit in the bucket.
What does Evenwood notice about the bucket as he assesses it and the size of the group? Question for the DM. Do I need to role a perception check?

Nix helps Alecia in and joins her

The crowd at the bar part allowing Sue to pay the fee effortlessly and return quickly to the Transitory Band of Wayward Acquaintances.

Meanwhile the band view the well perhaps with a mixture of curiosity and apprehension. The top of the 40’ diameter well is ringed by torches, providing light for the first fifty feet or so down the well before a plunge into the darkness of Undermountain. A beefy block and tackle mounted on a swing arm is used to lower and raise folk in the well’s bucket. There is a bell-rope that hangs down the side of the well so that the bell can be sounded to signal a return from the dark depths.

Evenwood appraises the bucket, perhaps almost 2.5-3' in diameter and the same n height. Probably completely stable and safe for one medium sized humanoid to sit in or two small sized people to stand. Two medium sized humanoids could stand in the bucket with some level in instability. Three would fit in at a pinch but could be rather unstable.

Nix starts to help Alicia into the container as two of the nobles march round to operate the winch.
"Decided your 'marching order' already, yes?" queries Regnet.

The crowd start to abandon the bar and form a circle around the well. They break into song, good and less so voices all mixing with gusto,
"Down, down, down the well!
"Strappen up and sharp thy blade!
"Down, down, down the well!
"Oh strapping lad or 'venturer maid!
"Down, down, down the well!
"And back again, once Durnan's paid!"

Sue clears his throat. "If you would allow me to secure the landing?"

Regnet looks at Sue and then at the pair who, between them, have one elegant leg already in the bucket.

"A sidebar to determine descent order might be in order?" suggests Jim. "Someone, or a combination of someones, that can secure the landing while others are descending does seem prudent. While the... rideable... area of this contraption seems fairly limited, I can always balance on the edge while holding to the ropes if we need more than two on the first descent. Personally I would suggest someone that can take a hit and another that can heal be the first ones down." Looking down at his own slight frame he adds "I prefer to avoid the first where I can and can not do the second."

"I believe I can foot that bill. If you'd allow me good wife." He winces again at the watch slang that slips out.

"Then I suppose that leaves me as the Second." Brushing Nix's arm she slips into bucket with someone approaching ease, her tall frame bending in ways she had forgotten. "I will see you all down there." Drawing the Crossbow that hangs at her side she notches a bolt and prepares to move.

Nix watches nervously as Alecia's descent.

[lol, would have done things differently if i'd know the bucket was 1-person sized :/ ]

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1 person medium sized can sit safely. 2 medium sized can stand with slight risk of instability.
I think Sue plans to descend with Alecia..