Akkron sighs. He thought that he had been as clear as he could when voicing his theory. Oh well.

"Alright... I suppose I'm ready to move on as well. Best not to linger too long in one place."

Dab nods as everyone discusses the situation, but is quick to remind himself that, experts or not, they're all speculating with limited information at the moment.  He resumes forward movement, watching for threats again, and this time especially dialed in for any funny lookin' rocks...

Slip keeps an eye about and above for any threats while moving forward with the group.

As you enter what would probably be a town center the ruins  become somewhat more building-shaped. Except these seem to be mainly ornamental and clerical, with remnants of a high-arched ambulatory and twisty iron shrines, as if the village was run on alters and alms alone. Cover grows taller and shadows grow longer as the sound of windblown sand occasionally breaks the silence. 

You can make investigation/perception checks to explore I’ll say that you can take advantage if you split off from the group. Just know that if anything were to happen it would take an actions-worth of movement to reconvene. 

I say we keep together for now.

Perception 28

Akkron is also going to stay with the rest of the group, though he does call forth his little spider to assist him in scouting the area (the spider will take the Help action to give Akkron advantage on his Investigation check).

Investigation: 18

Using Knowledge from a Past Life to be a somewhat better investigator... add 3 to the above result

Perception 27 with advantage from shield for Lorlin 

Lorlin: Your shield swishes close to the ground, billowing a small trail of sand. While it doesn’t trigger any traps it does bring up cloudy chunks of glass.

Slip: With the sandy landscape changing you know to look for foof traffic evidence around corners and under cover.  While your search is unsuccessful you do notice burn marks at eye level on the rubble that still stands. 

Akkron: your spider runs a radial sweep. It dips up and down from sight, disappearing into the various religious remnants. It occurs to you that some features of this town could be (or at least could have been) underground. From your past life you know what a wealthy grave looks like and as you maneuver through the ornate gateway of a mausoleum you find your spider friend chewing on a dead body. Partially exhumed and fancifully dressed, it’s skeletal hands grip a half-filled bottle. 

"Well hello there, friend" Akkron says as he sees the corpse. "Somehow, I suspect that my companions and I will need that bottle more than you will... once I figure out what it is, at least."

The tattered finery adorning the body gives Akkron a moment's pause, as he considers the possibility that he might be looking at another lich or similar undead being in a restful state. But he quickly dismisses the idea. Even a humble zombie would have almost certainly reacted to the Fey spider gnawing on it's flesh. Akkron carefully peels back the corpse's fingers and removes the bottle, studying the contents for a few moments to determine what he's found.

Arcana: 27 (OG roll 26, probably going to change because I edited the post for formatting...)

Dabbert keeps his wits about him as they begin exploring the ruins.  He does his best to investigate the various things that his colleagues see.  Scorch marks.  Glass.  What sort of weapon or magic turned the sand to glass, or left the scorch marks on the buildings?  He looks for broken doors, destroyed walls, busted windows, burned homes...anything that would indicate signs of a battle or...well.  Whatever happened here.  Something that would give them clues about the size and capability of their enemy.  

"He uh...looks hungry."  Dab says when he finds Akkron and his spider, and sees the spider gnawing on the body.  "Do you ever feed that poor thing?"  

"I literally just summoned it into existence less than an hour ago," Akkron says with a chuckle. "Well, at least onto this plane of existence, I assume that the spirit probably existed before I called upon it. Don't worry too much, I'm quite sure that he's capable of feeding himself. "

Akkron takes a few more moments to study the contents of the bottle before he nods in satisfaction.

"Looks like our friend here took a Potion of Healing with him to the grave... a strange decision, and unfortunately I don't think it will do him much good. But it could prove useful for us in the unfortunate event that our Cleric goes down."

(DM told me what Akkron and his spider found in a private message)

(Your acquisition  was  probably full and may have been more effective at one time but between the devil’s cut and the angel’s share the fancy bottle is probably worth more than whats inside.)

(Still useful in an emergency to get our Cleric back up since she's the only one with healing spells...)

As you inspect from the outskirts inward the sky becomes darker. Ruins stretch higher until they cast long shadows from the rusty sky. You can start to see more definition in the reliefs and statuary growing more frequent. Depictions of joyless rulers and grotesque tortures seem to follow you with their eyes. 

 I’m going to need three rolls from you to flesh out what happens next: 

Perception, Stealth, and Initiative.

Perception: 17 (with Help action from the spider to gain advantage)

Stealth: 26

Initiative: 11

Perception 23

Stealth 30

Init 25

Perception:  27

Passive Perception is 19

Stealth @ Disadvantage:  32  35

Initiative: 25

Fifty feet away, the long shadows are interrupted by torchlight blazing from behind a stone wall The red glow flickers as the lights seem to be moving back and forth behind their 20ft long cover. A flabby arm hoists an unpleasant head over the 10ft-tall rampart to peer through glassy, unused eyes.  You all are not alone anymore. However, the topography and darkening skies provided excellent cover for sneakery and you could close the distance to strike  first, provided you remain silent and refrain from verbal communication.

(Thanks to your stellar sneak rolls, you can surprise these guys and take top initiative in a combat. If you want.)

[Dab.

Slip.

Akkron.

Tess.

Torch 1

Big Guy

Torch 2]