Kileprat your spidey or Kiley? Sense tingles and you catch the bolt and break it.

Thug leader: Sh#@

Order: Thug Leader, Thug Group 1 Aino, Storm, Thug Group 2, Thug Group 3 Kileprat, Casey, Thug Group 4

Thug Group 1 is ahead of you ne t to the leader.

Group 2 is to your left on the roof 6 total

Group 3 right 6 total

Group 4 behind 4 total.

The leader will charge Casey and attack.

He gets to attack 3 times. Two with his scimitar once with his dagger.

2 miss 1 hit for 4 damage.

Thug Group 1 will charge the party . The 3 will split up and attack 1v1.

Thug vs Aino: 2 attacks both miss

Thug vs Kileprat: 2 attacks 1 hit 3 damage

Thug vs storm: 2 attacks both hit for 13 damage

Aino and storm up

Aino begins humming a tune and enters her bladesong. as a bonus action.

As an action, Aino pulls out the tiniest bit of spider silk in her fingers and whispers in Elvish, "Remba", casting and concentrating on Web:

60' range.  4 x 4 squares (20' square).  Trying to cast it on a rooftop to entrap all 6 of one group of crossbowmen (group 2?)
- Every turn they start or enter there (which I'm hoping is every turn they are on the roof), they must make a DC 15 DEX save or be restrained
    - restrained means 0 speed, disadvantage on attacks and attacks against them have advantage.
    - They can use up their action to make a DC 15 STR check to free themselves, but then at the start of the next turn, must make the DC 15 DEX save or be restrained again, as long as they stay on the webbed roof.
    - Area is also difficult terrain.
    - Goal is that every turn on the webbed roof, they keep having to make the DEX save at the start and keep getting restrained
    - They can set fire to the web but then it takes their action and they take damage.

(Let me know if it looks like it's not going to work that way at all because of the layout, because if so, Aino might have done something different).

Thumbtack flies by the face of the thug leader, granting advantage to the next attack against him by anyone.
Edited to add:  per the retcon in post 528 below, Thumbtack's help action is against the thug in front of Storm, not the thug leader.

Quote from Tybard >>

Aino begins humming a tune and enters her bladesong. as a bonus action.

As an action, Aino pulls out the tiniest bit of spider silk in her fingers and whispers in Elvish, "Remba", casting and concentrating on Web:

60' range.  4 x 4 squares (20' square).  Trying to cast it on a rooftop to entrap all 6 of one group of crossbowmen (group 2?)
- Every turn they start or enter there (which I'm hoping is every turn they are on the roof), they must make a DC 15 DEX save or be restrained
    - restrained means 0 speed, disadvantage on attacks and attacks against them have advantage.
    - They can use up their action to make a DC 15 STR check to free themselves, but then at the start of the next turn, must make the DC 15 DEX save or be restrained again, as long as they stay on the webbed roof.
    - Area is also difficult terrain.
    - Goal is that every turn on the webbed roof, they keep having to make the DEX save at the start and keep getting restrained
    - They can set fire to the web but then it takes their action and they take damage.

(Let me know if it looks like it's not going to work that way at all because of the layout, because if so, Aino might have done something different).

Thumbtack flies by the face of the thug leader, granting advantage to the next attack against him by anyone.

 Good move stands at described.

Thug that hits Kileprat will get a smack from Last Quip. 

To Hit: 13 Damage if it hits: 15

Kileprat hit. This guy is bloody but still standing

OOC: I will post Storms turn in the morning

Is it ok to retcon something for Aino?

I misread which thug attacked who.  I thought the thug leader had attacked Kileprat or Storm.  But it looks like they attacked Casey?

Aino wouldn't be sure if Casey is going to attack or maybe cast a spell with a saving throw, so she wouldn't have Thumbtack take the help action on the thug leader as I had written.  She would have the owl take the help action one of the others, let's say the one attacking Storm.

Is that all right @DM?  If so, then Storm, if you attack the one in front of you, do so with advantage.

DM: sure no issues storm has advantage if he attacks the thug in front of him

Storm grits his teeth as the thug hits him, he emits a low growl as he casts a spell, "You are marked for vengeance!  You dishonorable bastard!"

Bonus Action:  Casts Hunters Mark spell and chooses the thug in front of him, it adds d6 damage on weapon attacks and if he dies I can choose a new target as a bonus action.

Shatterspike Attack w/ Adv: 27 to hit (I rolled a 19 on both dice...) Damage: 13 total

You hit and the Thug is hurt but still in the fight.

Order: Thug Leader, Thug Group 1 Aino, Storm, Thug Group 2, Thug Group 3 Kileprat, Casey, Thug Group 4

Group 2 is up. They will make their Dex saves.

All but 2 fail. It's pure chaos on that side. They attempt to shoot at the party with crossbows and all miss.

Group 3 will also shoot at the party. 5 of the 6 miss the 6th aiming for Aino ro.led a nat 20 hits for 17 damage 

Kileprat and Casey are up

Kileprat will swing at the same thug she hit before.

"Well, heres one thats already sorry they started this fight."

To hit: 14 Damage: 17

Hit. You are able to maneuver your sword and bring it down on the Thug's neck, cutting him down. 

As a reaction to the crossbow bolt aimed straight for her throat, Aino speaks another word in Elvish and jagged Silvery Barbs of light spike out towards the crossbowman, distracting them, and in other directions.  Aino now also has advantage on her next d20 roll.

The crossbowman who got a nat. 20 must re-roll their attack on Aino.

Casey casts Dissonant Whispers on the thug leader, for 14 points of damage DC15 Wis save for half-  also if he fails the save he must use his reaction to run away from her.  

If he makes this save, she uses cutting words and her last bardic inspiration to subtract 3 from his roll if it makes a difference.  If no she holds her inspiration. 

if he runs, she moves back away from the fight and gets cover.

Also, @Nontyper - did Kileprat rage?  I am only asking because it might affect who Aino gives advantage to with Silvery Barbs and her familiar later.  I am assuming Kileprat is raging, and I think I saw you added the +2 to damage on her last attack.  Just wanted to make sure (I might have missed it).

The bandit lines up the perfect shot on Aino as he goes to pull the trigger he sees the barb flying at him. He ducks as he pull the trigger sending the bold over Aino's head. Miss on a 17

(So essentially he has to beat a 20 Wis save) 

Quote from Tybard >>

Also, @Nontyper - did Kileprat rage?  I am only asking because it might affect who Aino gives advantage to with Silvery Barbs and her familiar later.  I am assuming Kileprat is raging, and I think I saw you added the +2 to damage on her last attack.  Just wanted to make sure (I might have missed it).

 Yes, thought I added it.  I checked it on character sheet and added the +2.  Have now edited my post to include rage.

The Thug leader rolled a 19. You use cutting words and the inspiration riding it to 14. She starts to run. Any with a reaction left gets an AOO. Also his men see there leader running and will make a wis safe on their turn DC 13 or flee

Aargh, that is so awesome by Casey, so it is killing me that I have to point this out (unless there is a pre-agreed rules adjustment?):

Rules as written, a College of Lore Bard's (so Casey's) Cutting Words feature cannot be used to reduce an enemy Save:  "When a creature that you can see within 60 feet of you makes an attack roll, an ability check, or a damage roll, you can use your reaction to expend one of your uses of Bardic Inspiration, rolling a Bardic Inspiration die and subtracting the number rolled from the creature’s roll."

By contrast, a College of Eloquence Bard's Unsettling Words feature can only be used to reduce an enemy Save:  "As a bonus action, you can expend one use of your Bardic Inspiration and choose one creature you can see within 60 feet of you. Roll the Bardic Inspiration die. The creature must subtract the number rolled from the next saving throw it makes before the start of your next turn."

I have played both bard subclasses extensively, so I have had this distinction hammered into my head.  On the other hand, if we want to go with "Rule of Cool," then I say, let it stand with Dissonant Whispers taking effect and the leader bailing out of there!