Insight check, especially on the tears.  20   Is this guy a con artist?

Oben reaches into his coin purse and pulls out the coin to buy Hilben and himself another drink.  Keep your coin, friend.  This one's on me.  He also takes care to secure his coin purse under the folds of his jacket so it would be very hard to pick.  He pays for the drinks.  An emerald crescent, you say.  Have you asked around town about that?  And how many bandits were there, from what you saw?

OBEN

Insight: The man seems to be telling atleast a partial truth, though Oben remains skeptical as part of his nature, and his tears also appear to be genuinely sourced.

"Thank you, thank you." Hilben says in gratitude, grasping for the handle of his newly gifted drink. "No, I just assumed it was some obscure syndicate, as I hadn't seen such an emblem before. . . and from what I could see, there were maybe five of the damned crooks, which was a larger party compared to what we were accustomed to." Finishing his response, the man takes a deep drink, and resumes his quiet sulking.

Oben tuts in sympathetic disapproval of the general state of things.  Sure, I'm surprised the Baron allows such lawlessness so close to the town here.  He has a reputation for keeping things under tight control, is that not so?

OBEN

"I don't know of the man personally, but I'm sure he's doing the best he can within his ability. He's been sending expeditions lately, I've heard, but - well, I presume that protecting his traders isn't the highest of his priorities. But what would I know of that rich business, eh?" Hilben responds, with no real answer to the question.

Of course, of course.  Oben will stay for a while with Hilben, getting directions to where his wife was taken, probing gently for anything the man missed in telling the story, and making absolutely no promises.  He then heads off to his room, double-checks his coin purse, and goes to Reghetyr's door to see what he can overhear:

Stealth: 17
Perception: 15

Then he goes to bed and sleeps.

OBEN

"I don't know where they were taken, but I overhead one of the bandits saying they had some hideout in a cove due West of the path. It might not be the most trustworthy information, but it's all I have." At this point, after three tall mugs of mead, Hilben is noticeable inebriated, and is unable to provide further corrections or information. Moving up to Reghetyr's door, you can overhear strange murmurings, and a faintly otherworldly snarl. Disturbed by the event, you head off to your fairly comfortable room, and go to sleep for the night.

REGHETYR

Roll a Perception check against Oben's Stealth roll. On a success, you hear activity, a faint shuffling outside of your door, however cannot identify the source of the noise.

VESPER, INSSOl

As you both remain in the tavern, and Oben and Reghetyr disappear upstairs, men and women are beginning to depart from the tavern as the hour becomes late, supposedly heading to their homes to sleep off the food and drink.

If Oben manages to overhear (I'll leave that to DM's discretion):

(Yes, Oben can hear the provided text.)

(My bad, I didn't notice your previous post)

Reghetyr's Perception check: 5

REGHETYR

You hear nothing abnormal outside of your lodging, and continue conversing with your patron.

Vesper decides that this is as good a time as any to purchase a room and go upstairs.

VESPER

You don't have to purchase a room, as the expenses had already been paid for by the Baron, though the lodging strikes you as quite comfortable, and you go to sleep for the night. (If you have no other planned actions.)

Oben sleeps, wakes in the morning before sunrise, and looks for breakfast.

Unless it's against the rules of the Inn, Inssol would have passed out on the stool where he sat the night before.

Vesper went to sleep in one of the rooms.

PART II - "THE EMBER PLATEAU"

EVERYBODY

The morning slowly rose upon the divided islands of Nedroatan, sunlight slowly seeping through every crack and crevice of the earth. As for the party, slumbering in the Inn, they would either awake of their own accord, or likely be jolted to consciousness by the provided alarms. The Dragonwing Inn was almost empty, as the nightly crowd of residents looking for jest and drink had long been swept to their own homes for a spell, preparing for their daily routine. The Innkeeper laid snoozing dismissively against their desk, a spilled river of ink barely flowing past their wispy gray hair. All of Olmkirk was quiet, for now.

However, Francis Saltonstall was a restless man, and sat on the frontal balcony of his manor, watching the slow rising of the sun. It was a calming endeavor, a humbling activity that aptly set a tone for the rest of his day. He sat there, enjoying a breakfast of biscuits and sausage, a clock situated on the edge of his table. Today would not be one without it's due worries, of course. The group of four explorers, hell, mercenaries he had hired previously still wandering through his mind. As he consumed his morning meal, the Baron contemplated their arrival - of course, this is where most hired parties fragmented and dissolved, as the promise of virtually free drink and bed for a night outweighed any sense of duty. Saltonstall considered each member. Oben, a somewhat roguish man, though with tempered manners - he clearly knew what he was doing, at-least socially. Perhaps there is an ulterior motive to his presence? Regardless, he will likely serve as an immediate asset. Reghetyr, the eccentric Dragonborn warlock, was certainly a more mystifying creature - eager to please, yet undoubtedly volatile. Inssol, the honorable Gnomish warrior was a little point of contemplation, as the Baron viewed him quite simply. He took a liking to the fighter, though paid him little mind, and in that sense, likely underestimated him. Finally, Vesper, the Half - Elven woman with her inherent magical powers. Lightly spoken, even curt, yet no reason for worry or distrust. The noble hoped that this expedition would hold some fruit. Finished with his breakfast, the man stood, dismissing a servant who quickly moved to clean his dishes and silverware. No, Saltonstall thought, passing through the oak arch, back into his mansion - there will be work to do today.

Innsol is snoozing soundly on the countertop, curled up in his robe like a cocoon. He jitters a bit, trying to get in a more comfortable position, and falls.

"WE'RE UNDER ATTACK! MEN TO ARMS! BATTLE P-" he bellows at the top of his lungs, clutching his katana over his head like his life depended on it. Which it usually did. He stopped screaming once he realized he was still in the Inn. 

"Oh. Fancy that. False alarm."

Oben wakes early and heads to the common room.  Good morning, good innkeeper he says loudly into the innkeeper's ear until they awake.  Breakfast for myself and my fellows, if you please. 

Taking advantage of the empty room, Oben spreads out, sitting on one chair, his feet up on the back of a second, his pack balanced upon a third, and makes himself comfortable as he waits for the rest of the party.  At the sound of someone loudly shouting "WE'RE UNDER ATTACK" he raises an eyebrow and listens attentively for more, but hearing no sound of approaching hordes he relaxes and leans back in his chair.

OBEN, INSSOL

Upon being somewhat rudely awakened by Oben, the innkeeper shakes off the grogginess of the morning. "Yes, yes, apologies." He looked up towards the kitchen, calling out: "Reuben! Breakfast for four, Reuben!" And with this, slightly agitated, the innkeeper returns to his work, and begins to write a letter of conclusion to the Baron concerning the stay of the party. Meanwhile, some of the other early rising customers are beginning to filter down the steps, some outright leaving, and others seating themselves for breakfast. A young human waiter exits the kitchen. "Crumpets, ham and eggs comin' right up! Sorry to keep you waiting!"

Oben, roll a Wisdom (Perception) check.

Oben's Perception: 23