If X is some investment (gold, real estate, Apple Inc. stock, whatever), and I have structured my portfolio so that I would benefit from the price of X going down, then I am “short X”. If I would benefit from the price of X going up, then I am “long X”.
“You are naturally short housing.” = “If the price of housing goes down, you will be naturally be better off.”
“You are naturally short housing.” = “If the price of housing goes down, you will be naturally be better off.”