<Snipped quote by Guardian Angel Haruki>

Do I need to take additional dashes to reach the balloon?

<Snipped quote by XxFellsingxX>

Yeah, it's safe to say that you will.
The balloon is at D2.

<Snipped quote by Guardian Angel Haruki>

Okay. So do you want me to roll a Con check right now?

First for my clarity: How many additional dashes will Jub take?
Because if he takes more than 5, then the Con check will be needed.

<Snipped quote by Guardian Angel Haruki>

How many do you estimate he will need to take to reach the balloon?

<Snipped quote by XxFellsingxX>

According to my calculations, Jub will need 7 additional dashes to get to the balloon, starting from the ramp the normal dash got him to.

5 Additional Dashes will get him across the rocks (should the rolls for crossing the rocks be in his favor), and onto the middle of the plank pathway leading to the half moon shaped dock at D2. That dock is where the balloon is.

<Snipped quote by Guardian Angel Haruki>

Then he will take that many dashes.

(I'm sorry if I'm missing something and being dumb right now)

<Snipped quote by XxFellsingxX>

No worries! It's all good! ^_^

Now then, for crossing the stone steps.

I would like either a Nature Check or an Arcana Check (at disadvantage, because Jub's in a hurry).
Should that roll be a failure, I would like an Athletics or an Acrobatics check.

<Snipped quote by Guardian Angel Haruki>

I will do that.

Just one question: is the Lucky Stick still usable?

<Snipped quote by XxFellsingxX>

It is! It hasn't been 24 hours yet. ^_^

<Snipped quote by Guardian Angel Haruki>

Aight!

... oh no.

I got a 10.

Oof. That would be a Fail.
Go ahead and make that Athletics or Acrobatics check.

<Snipped quote by Guardian Angel Haruki>

Is this also at disadvantage?

Nope! This would be normal.

<Snipped quote by Guardian Angel Haruki>

Alright. Got a 14.

O_O...

That would be a pass. Just barely...!

So, Jub and Brutrumukk reaches the half moon dock, go ahead and make the two Constitution checks for the two additional dashes.

<Snipped quote by Guardian Angel Haruki>

Uh oh...

The first one is a 4... which given Jub had a +3 makes it a nat 1.

The second one is a 22.

Could Brutrumukk use the help action to give Jub advantage on the investigation check?