Laladak tells Gretchyn that there was someone watching the orphanage from the rooftops and he is going to be hanging around to protect the children abd make sure no one else disappears today. She replies she would be grateful for the protection. 

Meanwhile Tyris goes back to the rooftop where someone was spying on the orphanage. 

(How do you guys want to play this? Do you want to give me hourly perception checks, something else?)

Hourly perception checks work. Laladak is going to patrol the grounds and check on the kids in a steady cycle. 

(Hourly perception works for me.)  Tyris watches from the rooftop, staying in the shadows; bow in hand, but not drawn.

First our:

Stealth: 9

Perception: 24

Laladak is not trying to be stealthy. He wants people to know these kids are under his protection. 

First hour 

Perception 13

I assume the party left the Inn around 9am and spent about two hours getting to the orphanage and talking to Gretchyn, climbing up and down roofs. So it's now around 11am. You are going to meet up with the rest of the group for dinner at the inn, lets say around 6pm. So that is 7 hours to watch the area and protect the orphanage. 

Nothing of interest happens the 1st hour. 

Each of you give me 6 perception checks one for each hour. If something of note happens during one of those rolls, the following rolls will be void.

Perception 1: 22

Perception 2: 8

Perception 3: 11

Perception 4: 18

Perception 5: 23

Perception 6: 25

do you want me to do stealth checks too?

Perception  1:  16

Perception  2:  16

Perception  3:  24

Perception  4: 18

Perception 5: 5

Perception  6: 5

Perception 12

During the 3rd hour both of you see someone watching Laladak making his rounds. The person is now on a different rooftop than before. It's the square dark brown building about 80ft below where Tyris is and 120 ft from the orphanage (assuming each square building is 40 ft). The building is on Lantern St. and has ant right below it. Tyris gets a good enough look to see that the watcher appears to be an elf or half-elf. 

Tyris watches the elf for a while, trying to determine what specifically the elf is watching, and if he shows any signs of moving or leaving.

He is watching  Laladak making his rounds, guarding the orphanage and does not show signs of leaving 

(Have I seen him look in my direction?)

Quote from VanderLegion >>

(Have I seen him look in my direction?)

Tyris attempts to sneak down off the roof (on the side facing away from the elf), then move around and sneak up onto the elf's roof from the side opposite the orphanage, trying to catch him by surprise.

Stealth: 24

(This seems like a decent time to roll a perfect stealth roll)

He is obviously to your movements climbing down and across the street.

Give me a a climb check. Below 10 he hears you climbing up. between 10 and 19 make a 2nd stealth check to see if you climbed quietly.  20 or above you get to the top of the roof undetected. 

Acrobatics (climbing): 22

He is obviously to your movements climbing down and across the street, and as you quiety climb up to the top of his building, he still doesn't seem to have noticed you. 

He is an half-elf with leather armor and a sword on each hip, with a short bow strapped to his back .His back us to you and he is watching the orphanage with a spyglass  

(Do I need another stealth check if I want to cross the roof to him?  Debatig whether to try to get a sword to his throat or stay back with an aimed bow)

(No that 25 stealth will still be good since you made the climb check)

Slowly drawing a shortsword from its sheath, Tyris pads across the roof until he stands behind the man, then quickly steps up and puts his sword to the man’s throat, holding him from behind. “Tell me why I shouldn’t kill you right now.”  He says in a low voice in the man’s ear. 

(Ready an attack if he makes any threatening movements or tries to flee.)