Elwyn can't help but chuckle at the whole situation, but also feeling compassionate with the half-elf's predicament he offers his cloak to the young man. "Take this cloak good Sir and take good care of it, it has been through a lot I can tell you, but please tell us you're story now, I can't wait to hear it." Elwyn says to the man, trying his best to not burst out in laughter, while offering the man some bisquits from his backpack, along with some water from his waterskin. Persusion to get him to reveal his tale, with help from Ruby it would seem: 19 

Wake doesn’t have a cloak to offer, but he will quickly glance around from the elevated seat, especially the opposite side from the encounter.

Perception: 17

He will set the brake, hop down and approach the half-elf to ask, “Are you hurt? Is there anyone else here with you?”

All - The young man gratefully accepts the cloak, the biscuits, and water from Elwyn. "Thank you, my name is Daveth." He turns around, facing away from the group and fastens the blanket around his waist, then throws the cloak over his shoulders. He turns back to face you all and uncorks the waterskin, taking a long draw, then quickly begins eating the biscuits. Between mouthfuls of water and food he will say, "I am not hurt and I am alone. I'm from Amphail." He sighs and smirks ruefully, "Truth be told, this was supposed to be my first quest. Growing up in a small village, looking after other people's horses and watching them get rich while everyone else struggled day-to-day was not the life I wanted for myself. My father used to tell me stories at bedtime about heroes and villians, treasure and danger. I've heard the stories about Bandits in the area and figured it was time someone did something." At this point Isadore returns with a sack and some of his spare clothes. "Here's some food and something to wear. You won't win any beauty contests, but you'll be covered. Mostly." Daveth puts on the ill-fitting clothing and continues, "I saved up enough coin to buy an old shortsword and a leather cuirass. I set out to find the Bandits, but quickly learned that the world beyond Amphail is not quite like the bedtime stories my father used to tell. After a few days of sleeping in the dirt and eating dried foods, I was ready to give up and go back to raising horses. I started back the way I came when I found some clothing laying near the road that wasn't there the day before. I drew my sword and entered the woods. About fifty yards from the road was a pool of water. A woman was swimming. She must've heard me coming because she was looking right at me when I saw her. I apologized and said I saw the clothes and thought someone might need help. She smiled and tossed her wet hair over her shoulder, then began wringing it out. I'd never seen someone so pretty in my whole life. Then she invited me to join her and well..." His cheeks grow red again, "I wasn't thinking with my head by that point. I undressed and waded in to join her. She smiled and then dove below the water. When she surfaced she was holding a loaded crossbow. There were two others with her, I didn't even hear them come out of wherever they were hiding. They took everything I had and left me naked in the water. That was yesterday about mid-day. You're the first people to actually stop and offer any help. Thanks again."

Wake -

Kulogall hops down and says “Thank you, for telling us the truth.  That is hard sometimes.  We will be on the lookout for these bandits.  Beside the woman that you had a very good look at, do you have a description of any of the others?  Did you detect any accents, where they could be from?”

After hearing his response, Kulogall says “Fare you well sir, and don’t give up the adventuring life.  You just need some training.  And a healthy dose of, what is it… skepticism?  So that you won’t be taken advantage of by half naked strangers who seem harmless.”  He gives a half grin/smirk, pointing out the irony of the situation and his response to their caution.  Kulogall climbs back into the second wagon and sits.  

Kulogall - Daveth says, "The woman in the water had brown hair, fair skin, and pale blue eyes. She must've been an elf because her ears were more pointed than mine." His face takes on a far-away look as he recalls their appearances. "The other two were also women, one was a half-orc and the other appeared human from what I could see. The half-orc was very tall and grey-skinned. Her hair was very long as well, and she wore it in a bundle of dreaded locks down her back. The human woman had reddish hair in a bowl cut. They didn't have accents that I could tell. They spoke common well enough." Daveth's focus snaps back to the present. He actually smiles at the irony and says, "Thank you. I understand you were just trying to protect yourself and I apologize for my petulance. I believe you're right... Though my first real taste of the world outside Amphail was not at all what I had hope for, I'm still eager to find my place in it.

Elwyn smiles and chuckles as he hears Daveth's story. "Well Daveth, at least they let you go with your life. Consider yourself lucky being robbed by three beautiful and not so ruthless women then. And the best part is that this is a story you can tell your grandchildren after a long and heroic career as an adventurer." Elwyn says encouragingly, pausing briefly. "Perhaps you should come with us to Saltmarsh then Daveth. I'm sure the place holds adventure for us all, and I would be able to get my dear cloak back when you are done with it.", He adds, really hoping the best for the young half-elf, realizing he himself would probably do just the same mistake, and not even learning from it.

Elwyn - Daveth looks to you, an unsure look upon his face, "What kind of adventure? I thought Saltmarsh was just a backwater fishing village..."

If you like, you can make a DC 12 Persuasion check to try and convince him to tag along. You can make the check with advantage if another player posts that they also encourage Daveth to join.

"Oh no, that place crawls with adventure my friend." Elwyn says dramatically, not really knowing, just having a hunch. 
Persuasion to convince Daveth, the naive hero of Amphail to come along: 18 rolled with advantage if help is given, otherwise go with first roll.

Elwyn - Daveth looks away as he says, "I don't know... This is the farthest I've ever been from Amphail... and Mr. Luhan will need me around the stables." He looks back at the party, a conflicted look upon his face. 

Wake nods encouragingly to add Daveth to the troupe but realizes that the number of seats on the wagons is limited and that in reality, Isadore is the only one who could authorize another mouth to feed.

Would there be room to add Daveth to our party? Wake asks Isadore.

Wake - Isadore says, "If he wants to come along, we'll make room. We were supposed to have six escorts anyhow."

Ariana reaches in to her pocket

12

Ariana, sitting in the wagon, calls out to Isadore. "Well then, it seems this was meant to be."

Then Ariana addresses the newcomer. "Come, Daveth. You can squeeze between me and this triton. His name is Kulogall. I'm Ariana."

Kulogall begrudgingly makes room on the seat, gives an appraising look to Daveth, looking him over head to toe.  A little further, and it would have been like one examining a horse and looking at its teeth, but he didn't get that far in his appraisal.  "Have you any experience in a fight?  Did you learn how to use that short sword?  Have a seat and join us, although I'm not sure you will learn much from me, but you probably have plenty to learn from Ariana there.  Now, let's be on our way."

Ariana - Daveth turns red again, but you do see a bit of a smile on his face. He looks to you and the rest of the party and says, "Well... If you'll have me along then I suppose I'll come with. I'd like to repay you all for your kindness and... To be honest I was more than a little shocked by my encounter yesterday, but I don't want to let fear make my decisions for me. Thank you all. I will do my best to pull my weight." Daveth then starts to climb in the wagon, but he's still a little shaky. Isadore steps up and steadies him, "Whoa, there lad. Take it easy now." With Isadore's help, Daveth climbs into the wagon and plops into the bench seat. "I don't think Kulogall will fit up there with the two of ye, he can sit up front with whoever. I'll walk for a bit, my rear was gettin' sore anyhow." Isadore lets you all figure out the seating arrangements, then the caravan begins rolling down the road again.

Another few days pass and you all take your turns walking and chatting with one another. One evening around the campfire Daveth works up the courage to ask the party for lessons in combat and you all quickly learn that he has no skill whatsoever with weapons nor spellcasting but he's a quick learner and is in no way lacking initiative. He is a blank canvas to fill how you all see fit. Using the rules for Sidekicks in Tasha's, he can become either an Expert (Rogue), Spellcaster, or Warrior. I'll let you all decide amongst yourselves which direction his training goes.

”Well then, Daveth. Let’s see how you take to the path of a fighter.”

In the evenings Wake is more than willing to let Daveth hoist his shield and get used to the weight and swinging capabilities of his war hammer. While there is enough light, he’ll also allow him some practice shots from his light crossbow. When needed, Wake will use Mending to repair damaged bolts.

Wake will encourage, train and critique Daveth to the level of his proficiency. And always be ready with a Cure Wounds or Healing Word should he injure himself or others.

One evening, he even allows Daveth to try on his scale mail to gain some sense of its benefits and restrictions.

After few nights of watching Darveth improve after his training with Wake, Ruby decides she wants to join them. "Hey, maybe we can have a little training match, to see how you´d do in a actual combat." She says, drawing her shortsword as she walks up confidently and stands next to Daveth.

Her confidece plumets after realising how big their height difference is. She looks at Wake, now a little embarrased, her hand rubbing the back of her neck. "Or maybe not, fighting against me would´t help him much, would it. Forget I said anything." Ruby says and runs of. "God that was embarrasing!" She whispers to herself, deciding to rather look around their camp in a small radious for any signs of the bandits.

Investigation(?):21

Ariana is largely quiet while Wake trains Daveth. She was asked to help train him to be a fighter, and she wants to be a team player. Occasionally, when boredom lets her forget herself, she speaks up and straightens Daveth's arm here or corrects his footing there. Otherwise she lets Wake take the lead and mostly watches.

In a private moment with Wake, Ariana says, "You're a good teacher, Wake. My teacher is great, too. His name is Bravid Nan. He used to be a talented monk adventurer. I wouldn't be surprised if Elwyn over there has a few over-the-top stories about him. Anyway, I'm no teacher. I still think of myself as a student."

"I am excited to prove myself, though." And she pulls out her quarterstaff, performs a flourish, twirling it into a stance prepared for a fight, staring intently at an imagined foe in the woods. Then she relaxes and sits again.

Kulogall knows a little about the the use of a spear, which is unusual for a sorcerer, but it was a preferred weapon where he grew up, a spear or a trident.  He and his brother used to have competitions of who could throw a spear the farthest and the most accurate.  That degree of what he knew about fighting with a spear he taught to Daveth in hopes that it would serve him well.  

One night when they had traveled far enough with the wagons, after creating a campfire, Kulogall sat near Daveth and told him of his magical powers.  “I don’t know how I have them, but they seem to be growing.  One way that I can communicate with you if you are up front scouting is a spell where I can silently speak to you in your mind, and then you can reply to me.”   Kulogall demonstrates by sending him a message, “Like this.”  He demonstrates this and his other skills to Daveth (and anyone sitting nearby) so that they know what he can do.

"That's the spirit Daveth, and once again a fair woman has lured you into trouble." Elwyn says jokingly and winks at their new companion as he climbs up on one of the carts.

During the days Elwyn continues his taletelling but also takes an interests in the others and their reasons for travelling to Saltmarsh.
During the evenings he will applaude any progress Daveth does with his training, letting others, better suited for it train him.
He also brings out his lute, at least once per evening, mostly singing ballads about brave adventurers, fearsome monsters and fantastic treasures.
Occasionally he shares some of his more newly composed songs.

"There once was a young man from Amphail
who one day set out on his own trail
but a lass in a pool
made of him a fool
though being a hero he won't fail"

Knowledge to know stuff about Bravid Nan: 1 if he fails he will surely come up with some interesting story anyway ;-)