@mechajutaro said:

Refresh my memory; when did this happen in the first movie, and was it Wick himself putting endangering himself as such? Only place I ever recall him sleeping was his house, as Perkins accosted him in the hotel before he ever got a chance to saw a z or two

It was the scene where Marcus is about to shoot him in his bed and Perkins arrives, and of course, the bullet hits the bed instead.

Who in their right mind doesn't at least close the curtains when people are out to kill you? If he was world class, the bed would be positioned out of the view of the window.

Marcus shot the pillow so Wick would wake up and wouldn't be ambushed by Perkins. He might have kept the window open because of the Continental's rule of "No Business on Premises," also it's a movie.

maybe he just needed a bit of air...

My rationale was definitely that he was on the Continental grounds, so no business allowed. Plus, as stated above, the pillow was specifically shot to alert Wick of Perkins' intrusion in the room.