Keashirryl nods to Olan, as a sign of understanding more than enthusiasm. "You go ahead, I will follow from a little more... significant distance. Otherwise, I might catch their attention."

This clattering piece of metal will be my death one day, she thinks, running her finger along a crevice on her breastplate. Ironic.

[In this case, do I still need to roll for stealth?] 

Mud and Olan both slip out of sight into the alleys between the buildings.  For the moment, the 3 Redbrands keep their attention on Droknin who seems poised and ready to spring into pursuit after them.

(Who do you follow?  Eventually, the younger man turns and heads in the direction of a large tavern on the east side of town.  The other two continue down the road and up the hill, toward the ruined manor/keep.  If Keashirryl and Droknin follow, I need to know if you try to remain unseen, which will require stealth rolls, or if you plan to follow in plain sight while the others sneak around unseen.)

Mud will follow the other two going down the road and up the hill, expecting Olan to do the same.

Droknin realizes what his companions are trying to do. He resumes a standing position, crosses his arms, and grins. (Since he got the attention of the Redbrands, he will keep them onto himself. So, he’s just standing there pretty for now)

(Sorry for the delay on posting.)

Keashirryl sees the events unfold, and decides to stay with Droknin, in plain sight. She stays silent, not quite ready to talk about what just pursued, and follows the group - or at least the members she can see - with her eyes, making sure to note where they turn or continue their way. 

(Individual rolls.  If you're really serious about being sneaky, send the sneaky ones in ahead.  That can be a pain, but DM thinks using party average devalues the utility of characters that have chosen stealthy builds.)

Mud and Olan follow the two older Redbrands to the bottom of the hill that leads to the decrepit Tresendar Manor, ducking in and out of alleyways to remain unseen.  From the bottom of the hills, the path becomes circuitous, winding back and forth and around as it works up the hillside to the manor house.  The two humans follow the path but Olan and Mud are able to keep up and remain unseen by cutting straight up the hillside through the trees.  At the top, the men give a final look back down the hill at the menacing Leonin, before climbing in through a partially collapsed door.

You can overhear the sound of their movement inside for a short while, but then all goes quiet.  Do Mud and Olan follow them inside?

No, Mud will sneak over to a window that seems open and attempt to spy through it to see what's inside without getting spotted.

As Droknin looses sight of the humans, he will slowly follow them, but only to the bottom of the hill. He will wait for the others to report their findings.

While he waits, he sniffs the air, and then inspects the area for tracks. Maybe he can have an idea of how many people might be in the manor.

Droknin Survival: 21

Quietly peeking in through the missing windows of the ruined manor hall, Olan and Mud do not see any sign of the two men.  The interior of Tresendar Manor is a pitiful mess.  No furniture remains, but the floors are nevertheless covered with loose bricks and fallen plaster, debris, and refuse from decades of squatters.  Portions of the ceilings are collapsed, and a few plants and small trees are struggling to grow in those places where sunlight reaches inside.  A staircase to the second floor is missing the bottom flight of stairs and would need to be climbed... though you're not sure the upstairs would support your weight even if you made it up there.

There is a path through the refuse and the rubble, leading from the open front door to a lower staircase, leading down into darkness.  Unless they are hiding from you somewhere else inside, the two men must have gone down into the cellar.

Droknin, you sniff and inspect the road at the bottom of the hill.  For an abandoned manor, there is an awful lot of foot traffic going up and down the hill. You'd guess perhaps 15 to 20 men are regularly using this road.

Mud looked over to Olan. "Do we go down, or wait for the others? I'll let you decide."

"There are few advantages and disadvantages no matter what we do. Of we wait, we'll have more backup, but stealth will be out of the question. If we go no, we might be able to sneak around unnoticed, but it'll just be us." Mud ponders what to do. "Waiting has a higher likelihood of survival, but going now may prove more fruitful, since we may gleam more information by ourselves. I have no qualm doing either, so I'm letting you decide, and I'll follow without complaint. If you can't decide, listen to your gut."

(If Keashirryl is close to Droknin.)

Drokin inspects the ground at the bottom of the hill of the manor. His body tenses slightly. “I track about 15 to 20 humans ma’am.” The Leonin reports to the Cleric. “We should inform the others.” He will stay crouched, and waiting for her response.

While he whispers with Mud about what to do next, Olan catches a tiny glint that shouldn’t be there.  He looks again… and there it is.  Through the window and across the room, he spies a thin wire running across the top stair.  It doesn’t look like enough to trip someone.  Following the wire, he see it connects to a cluster of empty glass bottles at the top of the stairs.

Keashirryl followed Droknin to the bottom of the hill, and heard, not without surprise, his words to her.

"That lines up with what the old man said - the one we pissed off quite effectively. He mentioned something about outnumbering us. So, it is probably safe to say this is their main residence." she half says to Droknin, half pondering aloud.

She looks around for any of the Redbrands stationed around there or a patrol approaching, assuming there might be guards. (Perception: 18 ) 

"So that they don't walk into them?" she asks after the second statement. "Good idea. But how do we know we won't direct any unwanted attention to them?"

 [I'm sorry about the late reply.]

"I believe that the chance of their presence being revealed outweighs the danger they may face separated from us. I would like to suggest that we stay together, if possible, since our quarry is aware of our presence." Droknin is used to be a loner, but he now feels responsible for the safety these individuals that he just met. "I suggest that we find the others, and then decide on how to proceed." He will wait for Keashirryl's response before taking any action.

Keashirryl, you don't see any guards.  In fact, this whole side of town is pretty quiet right now.  Looking back, you can see townsfolk outside in the town square, likely discussing the dragon sighting from earlier.  But here the street and the hillside leading up to the ruined manor all look empty.

"Alright. I suppose it is best if we go. If someone is looking, they probably noticed us by now. Not that I see any sign of that..." she shakes her head. She is constantly evaluating the events, but nothing seems to add up, causing her increasing frustration. Then, she will follow Droknin up the hillside.