"The features seem... possibly familial of a sort?" says Chipper. "They look like Strahd's but not quite." As Kess goes to grab the portrait he nods silently, pondering this thought.

There is nothing on the back. 

A hallway with a window at each end wraps around the staircase railing. Framed portraits and mirrors festoon the walls, surrounding you with judging looks and dark reflections. You hear something scratching at one of the five doors. Three of them are locked, including the one with the scratching behind it. The other two have somewhat normal one person bedrooms behind them.

Kess avoids the two unlocked bedrooms, assuming they belong to the brothers. She frankly doesn't want to know what they do at home. Approaching the locked doors, she tries to lockpick one of the ones that doesn't have scratching behind it. They'll likely have their hands full with the sister once they let her out, so might as well search the other rooms before then.

Thieves' tools: 12 w advantage from sleight of hand + 2 proficiency= 14

The door swings open. Across from the door, a fire sputters and struggles for life in the hearth, above which hangs a framed family portrait: a noble father and mother (who you recognize as Fiona), their two young sons, and a baby daughter in the father’s arms. The sons are smiling in a way that suggests mischief. The parents look like uncrowned royalty.

Wood paneling covers the walls of the room. A closet and a framed mirror flank a curtained window to the south. To the north, a wide, canopied bed lies pinned between matching end tables with oil lamps. Stretched out on one side of the bed is a man dressed in black, his eyes each covered with a copper piece. He bears a striking resemblance to the father in the painting. Upon further inspection, you realize he's dead, but he hasn't been for long.

Kessintra is too distracted by the oddly happy family portrait as she enters the room to notice the body at first. When she does she freezes for a moment before relaxing once she realizes he's not in a state to do anything to them. She gives a nervous chuckle, remembering her own earlier comment. "Hah, went crazy after husband died. I knew it. Think she's actually been sleeping in here next to the corpse?"

"How long do you think she was going to try to keep him like that? Are we supposed to be worried corpses could start moving again if not taken care of properly?  Is there anything we can do?"  This is where Razz wished he understood this region better and knew what to expect and what not to.  He wished the Morninglord would lend him some more knowledge so he could clear the confusion from his head on this area. Trying to shake those thoughts away he looks at the rest of the group that followed Kess into the bedroom, "Think we'll find anything on him or in the night stands?

"She knew the gentle repose spell according to Urwin. Must have been hoping to revive him. Too bad she didn't have a Revivify scroll like us. Ah...It's worth checking." Kess sighs and steps over to the corpse, reluctantly feeling inside its pockets for any belongings. "Can anyone tell what he died of?"

Sleight of hand: 18 

You can't find anything more than pocket lint.

Razz will look at the body to see if he can figure out what he died from.

Medicine Check: 21

Kess steps back to let Razz do his examination of the body. Meanwhile, she will check the nightstands for anything of interest.

Perception: 14

There's no bruising or any signs of magical harm. It wasn't any sort of violent death. Likely an illness of some kind.

The nightstand contains fine garments, including a black ceremonial robe with a hood. One cabinet holds a locked iron chest.

"If he died of an illness, is it possible she'll have some diamonds stored somewhere?" asks Chipper. "I assume that would've been her issue with preparing revivify, unless he gentle-reposed him too late. Possibly the chest there?" He gets out his thieves' tools for a quick check, but doesn't have the greatest luck.

Thieves' Tools: 2+3 = 5 //IIRC it's DEX + Prof. Not sure though.

"Perhaps you'll have better luck." he says to Kess and then turns to the closet.

"It's possible. She did seem to come into some wealth after taking over the town." The drow carefully attempts to lockpick the chest as well.

Thieves' Tools: 8 w advantage from sleight of hand proficiency +2 tool proficiency= 10 -.-

Chipper, make a DEX save.

[[ Welp! I kinda wondered if one might need to be made. ]]

Chipper DEX Save: 12+3 = 15

A small dart shoots out of the lock, but you're able to dodge in time. Kess, do you still want to try to pick the lock?

"Maybe it's safer to find the key. The thing might do something worse next." Kessintra will instead search under the bed.

Investigation: 9 -.-

Nothing under the bed.

“It’s a good thing we are all proficient with lockpicks. It’s bad that we all suck at it though.
NAT 1 lockpick — used my inspiration -> 18 lockpicking (16+2 prof). 

The lock opens. Inside you find a set of bones.