Then, I would like to have Kate and Lucia spend as many hit die as needed to get to full HP.

Whispering, Tomoe asks the girls Do we spring the trap? Or so we go out the window and go back in the front door?

Lucia, who had gotten up along with Kate sits back down and says, "Looks like they'll be busy out there for a while. Let's just finish resting. Then we'll sneak out the window and blind-side them from behind. Surely there has to be another window we can reach from the outside."

Lucia Heals: 6

Kate heals: 6

Does Tomoe want to use her hit die to top of HP?

(Double Post due to bad internet. Lucia's 6 heals her fully)

Kate heals: 8

Might aswell. 

8

I can't see your dice rolls but that's okay because even if you rolled a 1, it would have been enough to fully heal.

The rest of the... rest passes in uneasiness as there's an ambush right on the other side of the door. Having their wounds healed, Lucia stands up and opens the window. She puts her head out and looks outside. She points to a thin ledge and says, "There's a thin extension we can use to crawl along the building. The walls have a bunch of cracks for getting a better grip. You guys want to try to get to a window first or should I?"

DC13 Acrobatics. Fail and you fall off the ledge and hit the ground 20ft below. It probably won't kill but will do damage and alert other lowlifes to your presence

Is Kate compitant enough in that skill to attempt the climb down? Or could Lucia and I do it first and try to catch her if she falls ?

Funny thing is, Lucia has the lowest mod in that stat out of all of you. She'll get better with levels cause she'll be improving DEX before WIS but right now, she has the lowest bonus.

...ew. is there anything around we could use to to help? I know the DC isnt too high, but I need my team to be in top shape as long as possible.

If not, I'll go down first, then Kate, then Lucia.

Acro check 23

You could try rope. Lucia has +4 to Acrobatics so even without help she has a 60% chance of success. You could tie the rope to the barricade or something else that's heavy and then climb down with the other end to help Lucia pass her check.

We will try that. I rolled Tomoe's in an edit above.

Using the rope, Kate and Lucia try to climb down as well. (No advantage but the DC was reduced)

Kate: 10
Lucia: 12

That's an unlucky roll. Good thing you tied the rope. Kate effortlessly climbs down the rope and enters through the window on the first floor. Lucia attempts to get down but slips and almost falls. However she manages to regain her grip at the last moment. She breathes a sigh of relief and then finishes climbing down.

The room you are in is made of stone. You are back at the first floor. It has the faint smell of orc. There's a bunch of magazines on the floor and cheap, unframed paintings of orcish women in bikini armor adorn the walls. Some of the paintings have the remnants of the posters before it. Looks like these cheap paintings were stuck to the wall with glue. On the floor is also a bedroll and a pile of clothes that are too dirty to wear but too clean to wash. This must have been the orc's room.

What do you do now?

If Lucia falls, I will try to catch her to reduce any damage and noise her fall makes.

Proceed with caution to the other side of the room were the door is, staying as quiet as possible. Stealthily one might say.

Stealth check if needed for Tomoe 9

She doesn't fall.

Terrible stealth roll in above post.

Tomoe tip toes forward. She trips on a small stack of magazines and makes a crashing sound. There's gross sticky beer on the magazine. Tomoe's face is dirty now. So much for stealth. Opening the door, you find yourself back in the first floor. The door near the stairs that you didn't check the first time around had led to the room you climbed down to.

Tomoe does her best to clean her face. That room was gross. Alright, let me go first so they can crash upon my shield. Then we pummel them.

Tomoe goes first, hoping to ambush the trap.

As you go up you notice 5 enemies still facing the barricaded door for an ambush. There are two guards with crossbows, two holy knights and a Guard/Fighter. They have set up a small wall of cover using drug bags. Luckily they are not behind any cover from where you're standing. They turn around and quickly scramble to action.

Surprise Round: Tomoe

Tomoe will start this party off with a suprise crossbow bolt aimed at the back of guards head.

I am going to roll with advantage since they dont see us coming.

Attack: 19 Damage: 10

Tomoe then drops her crossbow to ready her sword and shield for the melee.

Kate rages: All enemies take 2 damage.

Kate Vs Holy Knight 1: 14 (Adv: 26) Dmg: 18

Lucia Vs Guard2:  10 (Adv: 20) Dmg: 5

Kate's Crit damage: 6

Lucia Vs Guard2:  23 (Adv: 11) Dmg: 3 (again)

Kate charges straight into combat. All the startled enemies turn to face her as a wave of burning aura engulfs them. She swings at the Holy Knight 2 and separates his waist from the rest of his body. Lucia also rushes forth and knocks the second guard out with a flying kick. The Holy Knight and the Fighter both are caught on the defensive.

WIS saves: Knight - 10
Fighter - 10

Tomoe's turn.

Tomoe comes in bearing down on the knight2.

Attack: 8 Damage: 7