Several times I've travelled with three to Chile, always one is a new purchase, the other two usually work + personal. And 2-3 smartphones and a camera, same flight. Never really had a problem. I guess if they all were BNIB they'd ask questions, but none of my friends have had issues with their gear or their shopping, yet it's usually a different story with places like Argentina or Mexico. They do ask in Chile about possible odd luxury items that stand out, like art or golf clubs, not so much about personal jewellery tho.