I'm going to head up the stairs.

I'm going to go into the tailor's

Stairs.

Don't want to make any unneccesary noise...

I'll climb the casks and head for the roof.

If I use the window I'm almost certainly immediately exposed to what's inside, and I don't know whether I want that. Then again, I could easily get trapped/ stuck in the vent. However, at least I should be able to observe without being heard.

I choose the vent.

Follow the shadow. DIE, BITCHES.

I'm gonna wait and exchange greetings.....it may be my beer delivery.

I'm confused. I'm at the Tanners? What is the Tanners? Like a tanning salon?

Anyways, I'll start with opening box #1.

Despare - Checkpoint #4. You stand on the edge of a small ravine. Tiny, shiny objects can be seen between the trees on your left, and there's the outline of a hut on the right.
Climb down the ravine and check the objects, or check out the hut?

I'm psyschic, shouldn't I knew what's in the hut? ;)

Let's go check out those shiny objects, I just love traps. :)

A tanner is someboy who works with hides and turns them into leather and leather products I believe.

I'm going to check out the treehouse. It might be a trap, but the chance of treasure and a good vantage point to check things out from outweighs the risk.