A Collection of Strangers on Walkabout

The plan is pretty simple: I jump off with the crossbow and rope, collect the girl, shoot the crossbow at the top of the tower and start climbing. If I miss high, Khaguran will need to grab the rope and tie it off. I will use focus for both the jump and the shot. I will use Spell-touched to slow my descent at the end. The rope and crossbow are prepared prior to the jump.

Quick question for the phantom: how big is she?

Some additional questions for the phantom:
1) This is a magic crossbow. Does the bolt care about weight? I mean instead of shooting the bolt/rope, then climbing, could we instead just tie ourselves off, then fire the bolt/rope and just let it pull us along? I wouldn't ask this question, except for the "magic" part.
2) Alternative plan: Tie one end of the rope to my Stick and the other end of the rope to Khaguran. I wedge the Stick on the parapet and Khaguran jumps, they grab each other, and I pull them up from there. Assuming they both weigh less than me, then this would actually be easier, faster, and not require as much uncertainty. And the rope might not be exposed for any longer, as I can just start pulling and I should be able to pull faster than either she or I can climb unassisted.

Rikia is a human woman wearing a simple dark brown hooded cloak. She's 5’, has tan skin, short (chin length) brown hair, and glassy periwinkle eyes. At the moment she is calling for her master her voice getting raw.

Zastan! Zastan! No... NO! Don't leave me like this. I don't want to be alone again. I can't...

OK, how about combining the two tactics:
- Skeeve makes the stick long so it will get stuck in the parapet.
- Skeeve jumps down to Rikia (I'm just gonna use that preemptively).
- Skeeve then shoots the rope at Khaguran. (The theory: Khaguran is willing, so it should automatically hit. I'm trying to avoid a dice roll.)
- Skeeve and Rikia then start climbing up the rope to get out of there. Khaguran, if he's strong enough, can pull at the rope, too, to pull us while we climb up.If we could communicate with Rikia, I'd just shoot her from here! :)

No. Changing my mind again. This is the plan I now recommend.
- Skeeve makes the stick long so it hooks the trap door and wraps his arm.
- Khaguran ties one end of the rope to himself.
- Khaguran makes the jump down to Rikia (said even though we don't know her name yet).
- Khaguran then shoots the crossbow rope at Skeeve, who is a willing target. (So it's hopefully an auto-hit.)
- Khaguran and Rikia grab at other and hold on tight.
- Skeeve then forces the stick to contract as quickly as possible, pulling them up as quickly as he can. I figure him being a full sized human, the combined weight of Khaguran and Rikia should be low enough to allow him to pull them both up quickly. If necessary, he will then jump down the trap door to finish the retrieval.

This is all assuming Khaguran is willing to make the jump.

But, since we have so little time, there is no time for whomever jumps and Rikia to climb. They must be pulled out extremely quickly.

Along that line, are there any heavy objects we can use to help with the pulling them up?

"Okay, I think I'm following, and it seems like a good plan. I'm willing to take the plunge; having the two lightest people down there seems smart, assuming our combined weight isn't too heavy to pull up effectively."

So my one round of actions will be to grab Rikia, then shoot the crossbow rope at Skeve. I might suggest, Skeeve could even jump down through the trapdoor as soon as the rope harnesses itself to him. He might act like a counterweight and yank us up several feet at once as he falls. Depending on whether the staircase down to the next (2nd?) floor is enclosed or built into the side of the tower wall and thus open to the air, you could even go to the top step and jump down to the floor again for another free several feet without having to manually pull us.

I can see how that might be a little tenuous though. Our esteemed DM can advise if that seems farfetched given the circumstance.

That would have been ideal, but I have to be right on the edge for you to shoot me, and the trap door is in the middle. So, I still have to get from the edge to the middle before I can plunge down the trap door. My understanding is that all the other staircases are purely internal. So I have to be on the roof

Also, I recommend shooting me first, then grabbing her. I'll wait a beat before running.

Khaguran walks over to the parapet, leans over, and calls to the woman, "Miss, we're going to help you up. Don't be startled by the rope." He hopes his laconic mode of speech doesn't hurt her chances of trusting him too much.

Skeeve securely ties his end of the rope around his waist and stands by the trapdoor. When he gets Khaguran's signal, he jumps down and starts running down the stairs.

Skeeve will roll to successfully make the jump without injuring himself. Then, regardless of success or failure, he will run/limp down the stairs to keep pulling up. He will stop when Khaguran either yells to stop or when he gets to the bottom. I assume no Focus because he just doesn't have the time. I assume standard difficulty, as there is nothing to make it at Disadvantage.