You follow the map to Umbrage Hill, the location of the midwife. 

Built on the slope of Umbrage Hill is an old stone windmill surrounded by an iron fence. A large winged monster with a spiky tail is trying to knock down the windmill’s front door. A woman appears in a second-floor window, waves at you, and yells, “A little help?!” watching to make sure that the creature doesn't fly up to her 

Jayson pulls his crossbow, loading it in one smooth motion.

”This is it, boys.  Time to go to work.”

/holding for Init to be instituted/

"Oah!  Jayson, I tell you, no, the world, that you must be the greatest bard in all the world!  No one sings songs like you!"  

He is smiling all the way to the midwife's windmill...and then smiles wider when he sees the winged thing trying to get into the windmill.  Still tired from the fighting back at the Dwarves' mine, he still charges into battle and begins to sledge the winged thing at the door.  

"Don't worry lady!"  Gor calls up to her as he charges and swings his maul.  "We'll sledge you next!"  

Kosef was about to say perhaps a more tactful approach would word better. But when Gor runs forwards he shrugs, "Let Milil guide us i suppose".

He will run forward as well, casting Sacred Flame as he pulls up his shield:

Dex Save 14 or 7 Radiant Damage

Biezdar however a little uncertain after last beating he took. Seeing Gor rushing without second thought Biezdar fallows.

If we are close enough to get in melee Biezdar will not yet grab his flail, and instead will try to grab the monster to not allow it fly.

If we are still to far for melee biezdar would grab Javelin and throw.

Biezdar shouts to Gor: "What happened to element of surprise Gor?"

Athletics roll for grapple (6+6=12)

Javelin throw 17+6=23 damage 5+4=9 (throw was made regular attack assuming 30feet range.

Gor, you swing down getting a good hit, but it barely phases the creature,

Kosef, as the creature gets hit by Gor, you cast your spell but the creature, now aware of the attackers, dodges it.

Biezdar, you leap onto the large monster and try and pin it down. The creature squirms but your grip is firm. The creature is Grappled.

'Orsen' and Jayson may take turns before the monster. 

Jayson scurries to within hand x-bow range and lets fly.

(Rolls via page : 17 to hit, 7 dmg)

He calls up to the midwife.

”Please bear with us, ma’am.  We’ll be right with you!”

Orsons first.instinct is to hide.

Stealth: 8

The creature will try and bite Gor, and claw at Biezdar twice.

Bite: To hit: 18, Damage: 5

Claws: To Hit, 17 and 9, both miss.

 Everyone is up

"Pardon me madam, but is there a reason this beast is trying to get into your home here?" Kosef is a little bit confused as to why the monster is so intent on getting in the windmill.

Persuasion: 13

Unless she says something drastic, he'll probably try to blast off another Sacred Flame: DC 14 DEX or 2 Radiant Damage

"I have no idea. Hunger maybe?"

If you would allow for Biezdar to impose disadvantage by Protection fighting style (reaction), then Biezdar would do that to protect Gor. 

Other than that Biezdar has now one hand on shield, and another grappling monster (i imagine he grabs monster by the base of his tail (near the buttocks, as i imagine it is not that spiky there yet).

Biezdar uses his action to try and kick the monster in the rear area hoping to hit some sensitive area. Unarmed strike 8+6=14 for 5 dmg.

He drags the monster moving it away from the house and from Gor. Just by the 10ft. to get out of reach so Gor can move freely and advance or retreat without provoking opportunity attack.

"I have some rope strapped to my backpack, anyone fancies to try and tie this thing?"

Reaction: Fighting style: protection - imposing disadvantage on bite against Gor
Action: Unarmed strike: kick - hit:8+6=14 dmg=5
Movement: Drag grappled monster 10 feet away from Gor and house.

Jayson levels his x-bow once again.

”Sorry, Biezdar.  I am lousy with a lariat and I flunked basic seamanship.”

Jayson fires again at the party’s assailant.

(Rolls done via sheet.  13 to hit, 3dmg)

/If possible, would like to move to gain or provide flank bonus/

Quote from Wakharashq >>

If you would allow for Biezdar to impose disadvantage by Protection fighting style (reaction), then Biezdar would do that to protect Gor. 

Other than that Biezdar has now one hand on shield, and another grappling monster (i imagine he grabs monster by the base of his tail (near the buttocks, as i imagine it is not that spiky there yet).

 I assumed this was the case already (hence 17 missing due to shield). That was disadvantage on Gor. 

Orson attemps to sneak around to the backside of the building.

Stealth: 12

* *sorry, Forgot the 5ft restriction. Was going to use thrown pebbles but at that point it's just an attack I suppose**

To help you need to be within 5ft of the creature. If you are willing to do that, Gor gets advantage as the last person to act.

Gor sees what Biezdar is trying to do, and throws himself at the creature, trying to grapple it. 

"Surprise?"  Gor says, confused.  

The grappled creature is now grappled? As far as I'm aware, there is no benefit to grappling a grappled creature, but I will say if it tries to break the grapple, it has to beat both of you (it rolls once, you both roll to beat the same role).

It hasn't got much interest in breaking the grapple when it can attack you both though. 

Against Biezdar: Bite, misses.

Against Gor, claw 1 (disadvantage from Biezdar) 7 to hit. Claw 2, 20 to hit, 5 slashing damage 

Kosef yells up to the woman, "Thank you so much for your valued insight!" he fires off a Sacred Flame. "Perhaps you could do us a favour and come down here so we can rescue you!?".

Sacred Flame: DC14 DEX save or 5 Radiant damage.

Persuasion for the woman: 21 .

"If you think I'm coming down with that monster outside, you are very mistaken!"