Pardot paces at the door pacing and meowing and banging into the door. After 2-3 minutes of begging eventually the door opens gently inwards and the cute little cat is met firmly by a broom as one of the occupants starts swatting and trying to chase the cat. "You want some food you best go earn it like we did you miserable beggar. Barely enough for us we sure won't be throwing any to the likes of you. Be happy we don't add you to the table!" She tries to shoo you away from the door before slamming it shut. 

If you continue to watch from the window you will see all seven seats become occupied. They eat in silence, hungrily grabbing pieces of almost raw meat with their hands and tearing into it with sharp teeth. The chase the food with gulps of dirty water and a few bites of the stale looking bread. Once the meal is complete they quickly clean the table and exit through the north door. You would be getting very close to your one hour mark by the end of this meal. Let's say you have about 5 minutes left by the time they are done eating.

Assuming Pardot the stray cat messages an update Ludolf informs the others of what he has witnessed. "What kind of creatures could this be?" 
History/Arcana to determine kind of sharp-toothed creature: '12 assuming help action from someone.

"Do you think we can make a silent entrance Daventry." Ludolf asks their guide. "We need every advantage we can get with these ceatures."

Triäsa also tries to think of anything she might know that could fit with these sharp-toothed creatures, while Ludolf and Klin are discussing the same issue.  (Arcana: 8)  Seeing Daventry preparing, she slips quietly up next to her.  She tries to keep her voice soft as she sings her encouragement to the woman, granting her Bardic Inspiration. (1d6)

When Daventry is ready to go in Ludolf follows her trying to assist her in any way he can.
Stealth if needed: 22 Perception if needed: 7 Investigation if needed: 8

Daventry nods. "Keep a lookout, if you see any watchmen give me a signal." She pokes her head around the corner, then slinks across, approaching the door at an angle to not be visible from the window. She quickly takes a look at the door, quietly checking that the door is locked, before removing her thieves' tools if necessary and attempting to unlock the door.

Stealth: 15

Investigation (Door: Trapped? Locked?): 23

Thieves' Tools: 19

Guidance on Stealth: 2

You know the creatures are not human but none of you are sure what exactly they might be. 

Daventry the door is locked but you quickly realize there are no traps or alarms. You deftly pick the lock and the door silently swings open. You enter into the dining room it smells of raw meat with pieces still strewn about the table. To the east lies a single door Pardot knows leads to a kitchen while a northern door leads to some sort of corridor. Both doors are closed the east one lies quiet while you hear the soft sounds of snoring coming from jist beyond the north door.

Back as a halfling, Pardot fills the group in on what he’s seen, and helps to guide his companion to sneak ahead and open the door. Once he sees the door open, and Daventry peering in, he quietly walks across the street to join ((stealth 9 + 4 self guidance since Daventry’s would have been used)), whispering as he points inside, “Back that way is the kitchen, but I didn’t see what’s past the north door.”

Triäsa will follow after the others, staying near the back of the group as she does not figure herself to be very sneaky. (Stealth: 22)  

Ludolf follows the others into the hovel, looking around for the tomes they seek, while ready to follow Daventry to wherever she decides they should go next.
Stealth: 15 Investigation: 9 Perception: 5

Quote from Goliath7723 >>

"Do you have any idea? It might be nice to know, befor we barge in there." Klin adds.

”I actually can send in a scout.” Pardot whispers, adding, “Though if we’re looking at a fight soon I’d rather keep the stars on my side as protection. Of course… I’d rather not fight at all if we don’t need to…”

"Save your stars Pardot, it might not make much difference what's in the next rooms as long as we take them by surprise, which I've read is half the battle, not sure about the other half, the book didn't say." Ludolf whispers to Pardot and the others.

"Shh. I've a hunch, though I'll regret what we will find if I'm right... We don't have the right facts to murder these folk in their beds just yet." Daventry whispers. 

Daventry goes for the kitchen, quietly opening the door... And looking for the source of meat. 

Stealth: 12

Perception: 4

(@DM: for future reference, what should trigger a new stealth check in an infiltration like this? Each new room? Each action taken? Odds are, the more rolls/shorter 'duration' of the check, the more likely that nat one is coming...) 

Inspiration on stealth: 5 

You all search the dining area completely and find just the remnants of the inhabitants last meal. It is a dirty room with bugs and flies starting to swarm over the bits of food on the floor and table. Other than this the area is pretty unremarkable and you do not come across anything of interest.

As Daventry opens the eastern door to the kitchen it makes a slight high pitched noise as it gently swings inward. Similar to the dining/common area this room is a dirty mess. On a plain wooden counter top lies the recently butchered corpse of some sort medium sized game though the exact species is far beyond recognition. There are a variety of fruits and vegetables in baskets which are in various states of decay as well a single loaf of bread speckled with mold. 

Ludolf -- You hear the unmistakable sound of multiple creatures snoring from the north door. There is no light coming from under the door.

(In general I think you need to make new stealth roll with any action/event that could conceivably break your current stealth. I do not think opening most doors or entering the next room has to result in a new roll. I am OK with you all riding an initial roll then I can either ask for new rolls or roll them for you depending on the activity. All that being said you will need to all make new stealth rolls when entering the North room if you decide to do that. Though I can see you are pessimist! The more rolls the more chances for nat 20! The current status on stealth is the group passed the initial infiltration check and nothing has triggered a new check yet so I have ignored the other rolls, sorry Triäsa)

(Also to be fair Daventry would still have the inspiration since the roll was not needed)

"Well, at least it wasn't human or gnome or something." Daventry mutters under her breath, having expected a butchered humanoid skeleton.

She quickly takes a look around for any trapdoors or the like, hopefully with help from Ludolf or another.

Investigation: 22 w/ adv: 22 

(If that second stealth roll didn't have to happen, then can I take back that inspiration dice I used? Or just use that roll and inspiration for the inevitable entrance into the next room? Also, have you seen my forum avatar and my history in this thread? :D)

If nothing is found, she'll prepare to go into the north room...

Edit: Copy on inspiration. Also whoops, Investigation is only +2, not +4 for Dav.